


Tumblr Ask Box Requests

by Mayalaen



Category: Supernatural
Genre: Adult baby, Age Difference, Age Play, Alternate Universe, Anal Fingering, Anal Gaping, Anal Play, Anal Sex, BDSM, Begging, Boy King of Hell Sam Winchester, Breastfeeding, Caning, Caretaker Sam, Caretaking, Choking, Chubby Dean, Cock & Ball Torture, Cock Warming, Common Cold, Coughing, Crossdressing, Crying, Crying Dean, Cursed Dean, Curses, Daddy Kink, Diapers, Dirty Talk, Dom/sub, Domestic Discipline, Double Penetration in Two Holes, Dubious Consent, Emotional Dean, Enemas, Episode: s04e17 It's a Terrible Life, Exhibitionism, F/M, Face-Fucking, Feeding, Felching, Fever, Figging, Fingerfucking, First Dates, Fluff, Food Kink, Food Sex, Fucking, Gen, Grace Bondage, Hell Fic, Homophobia, Homophobic Language, Humiliation, Incest, Infantilism, Kid Fic, Lactation Kink, M/M, Male Lactation, Manhandling, Mark of Cain, Medical Kink, Mpreg, Non-Consensual, Object Insertion, Office Sex, Orgasm Delay/Denial, Orgasm Denial, Paddling, Panties, Pegging, Praise Kink, Pregnant Sex, Prostate Massage, Prostate Milking, Psychological Torture, Psychological Trauma, Puppy Play, Rape, Reader-Insert, Rimming, Roleplay, Rough Sex, Semi-Public Sex, Sex Toys, Shaving, Sibling Incest, Sick Dean, Sick Dean Winchester, Slurs, Sneezing, Somnophilia, Sounding, Spanking, Speculum, Spitroasting, Subdrop, Switching, Threesome, Threesome - M/M/M, Torture, Total Power Exchange, Twink Castiel, Violence, Voyeurism, Watersports, Wincest - Freeform, non-sexual infantilism
Language: English
Status: Completed
Published: 2015-06-30
Updated: 2016-02-17
Packaged: 2018-04-07 01:20:35
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 40
Words: 61,591
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4244124
Author URL: https://archiveofourown.org/users/Mayalaen/pseuds/Mayalaen
Summary: <blockquote class="userstuff">
              <p>Due to the nature of the requests, please read the <b>* WARNINGS AND TAGS FOR EVERY CHAPTER *</b></p><p>These will be individual fics, not connected in any way with different pairings, different fandoms, and possibly a wide variety of kinks.</p>
            </blockquote>





	1. Chapter 1

***Full chapter summary and links down below.***

I held an Ask Box Requests Event on [Tumblr](http://mayalaen.tumblr.com/) after reading an article about writing by request. I wanted to try out some of the things mentioned, but I didn't know if I could do it, so this was a trial version of it. I asked that prompts be of any characters, situations, pairings, etc. Go wild with strange themes, have me write a personalized scene, a canon scene rewrite, crossovers, totally raunchy sex, or just ask for some gen fluff. Really anything, as detailed or as vague as they pleased.

I was hoping for truthful and constructive criticism about what I wrote for people. Tearing me down for no reason was not what I was looking for. It was more of a "Hey, did ya like it? Did ya hate it? Would you want to request a fic from me again?” The fics were all short-ish compared to the much longer fics I usually write. I posted them here and also on my Tumblr account with the tag [Ask Box Requests](http://mayalaen.tumblr.com/tagged/ask-box-requests).

The experiment was a success and I had a good time doing it. Thanks guys!

## Chapter Summaries

[ **1\. Chapter 1: Introduction**](https://archiveofourown.org/works/4244124/chapters/9603369)  
  
[**2\. Open Your Eyes**](https://archiveofourown.org/works/4244124/chapters/9603435)  
**Anon Request:** Cas fingering Dean while Sam's sleeping in the next bed. Dirty talk, D/s, aggressive Cas.  
  
[**3\. Tips to Make Your Girl Weak in the Knees**](https://archiveofourown.org/works/4244124/chapters/9609408) **  
**Anon Request: Dean/Cas -- kill me with adorable and fluff. Cas wants to date Dean. He reads about how to woo someone in a magazine.  
  
[**4\. Size Doesn't Matter**](https://archiveofourown.org/works/4244124/chapters/9610059)  
**Assbuttintheimpala's Request:** Twink!cas (maybe senior in high school) having a secret relationship with cop!dean (who's maybe like 30) and Cas is a total size!queen so he asks Dean to fuck him with both his cock and his night stick? If you could put in some humiliation/slurs like Dean telling Cas how much of a slut he is and commenting on his gape that would be awesome. Also maybe for the scene they're somewhere they could easily be caught? Maybe Dean had sneaked into Cas' bedroom in the middle of the night?  
  
[**5\. Do As I Say**](https://archiveofourown.org/works/4244124/chapters/9638649)  
**Curlysupergirl's Request:** Can you write a chapter about Dean with complete loss of control (maybe TPE) with Cas in charge? Like the first prompt with humiliation, but maybe this time Sam actually witnesses it (doesn't necessarily need to be sex).  
  
[**6\. Run Trip and Fall Chapter 2**](https://archiveofourown.org/works/4244124/chapters/9995909)  
**Anon Request:** I didn't know that you take ask-box request! Can I request you too? About J2(Bottom!Jensen) having rough-sex and hyper-sensitivity with crying!Jensen. Jared is very animalistic but with after-caring schmoop:) I love your 'Run Trip and Fall' so much, It can be same verse with that (Especially mentioned fisting thing). Sorry about long request. Always thanks for amazing works!  
  
[**7\. Filled Up**](https://archiveofourown.org/works/4244124/chapters/10403586)  
**Anon Request:** Could you write a Dom Dean where he keeps Cas filled with piss and cum all the time, and when not filled, he keeps him stuffed with dildos and/or random object's, and Cas loves it. Maybe lots of dirty talk/humiliation?  
  
[**8\. Dinosaurs and Cough Syrup**](https://archiveofourown.org/works/4244124/chapters/10519902)  
**Anon Request:** I really wanna read something cute and fluffy with baby dean (infantilism) maybe even sick dean? I like either cas or sam as the 'daddy' but it can be someone else. I prefer non-sexual, as for the 'setting' I don't prefer one over another, although I did enjoy Mr. Kitty's New Friend :) I also like it when a bit of the Adultness shines through like deans aware of what's happening but he needs it ya know?  
  
[**9\. Customer Service with a Smile**](https://archiveofourown.org/works/4244124/chapters/10673975)  
**Anon Request:** AU or canon. Sabriel. Gabriel is a problem customer always complaining about something so he can spend time with Sam.  
  
[**10\. Mommy**](https://archiveofourown.org/works/4244124/chapters/10692266)  
**Anon Request:** I'd love to read about pregnant!dean started leaking milk from his flat chest. Sam seeing that, totally got turned on and having sex. After giving birth, Sam watches dean breastfeeding their baby and then Sam gets emotionally overwhelmed by that (feeling how beautiful mother dean is) If you don't mind, I also love some domestic fluff about Dean being Mommy, like the baby starts calling Dean mommy?  
  
[**11\. Us Against the World**](https://archiveofourown.org/works/4244124/chapters/10721567)  
**Anon Request:** I would really like Sam and Cas using Dean like a toy, for their own pleasure. DP, cockwarming, holding his ass open to be fucked, but lots of love and aftercare at the end!  
[**12\. Lies and Break-Ins**](https://archiveofourown.org/works/4244124/chapters/10796093)  
**[majesticduxk](http://majesticduxk.tumblr.com/)'s (majestic_duck) Request:** ok, I have a prompt! if it so inspires you... something d/d with a punishment spanking, and Dean being the spankee. I prefer slash, but am happy for him to be paired with whomever, and you can take it where you want.  
  
[**13\. More**](https://archiveofourown.org/works/4244124/chapters/10833173)  
**[Anon Request:](http://mayalaen.tumblr.com/post/128004500299/i-was-just-on-archive-of-our-own-and-i-wanted-to)** I was just on archive of our own and I wanted to request something. Can you make cas have a gaping ass hole that never closes and that needs to be filled up with a butt plug all the time and when dean has sex with him he has to have something else.  
  
[**14\. Doc**](https://archiveofourown.org/works/4244124/chapters/10833716)  
**[HollyBlue2's Request](http://archiveofourown.org/comments/33697956):** Maybe some doctor!top!cas  & bottom!dean with restraints, sounding, latex gloves and some good ole dirty talking? For a scene, maybe they've got a basement kitted out with some medfet supplies?  
  
[**15\. Daddy's Good Boy**](https://archiveofourown.org/works/4244124/chapters/10865960)  
**[IShipItAllAndThenSome](https://archiveofourown.org/works/4244124/comments/35014910)'s Request:** I kind of wanted to prompt something along these lines, but then I wanted to do it myself, but I still want to read your take on it, so here goes. Can I have Dom!Cas/sub!Dean with daddy kink (Daddy!Cas), praise kink, spanking, maybe a little exhibitionism (fucking by an open window or in an office - maybe Dean Smith verse with Cas as his superior? - or at a BDSM dungeon), and Dean being shy about his panties because he's never told Cas about them before? Sorry for the babble.  
  
[**16\. Sick of Me**](https://archiveofourown.org/works/4244124/chapters/10935524)  
**Anon Request:** Sam/Dean. Dean gets turned on by being taken care of, since he's always been doing the one taking care of people, but nobody knows because he has this phobia about anyone finding out, even - especially Sam. I'm thinking maybe being sick and fantasizing Sam will care take of him would turn him on the most in my headcanon, because being hurt fighting monsters is something that feels like a badge of honor, but being sick is just something his dad made him feel bad about. So, Dean is sick and feverish and therefore emotionally liable, and gets turned on by being taken care of, and Sam figures it out. And maybe Dean has a bit of an emotional breakdown on top of this because I feel like that would be a cathartic moment for him.  
  
[**17\. Pregnancy Blues**](https://archiveofourown.org/works/4244124/chapters/10948259)  
**Anne's Request:** (After I posted Mommy - Sam/Mpreg!Dean) Can I ask for a other wincest fic with pregnant sex (mpreg!Sam, top!Dean),please?  
  
[**18\. The Mark of Freedom**](https://archiveofourown.org/works/4244124/chapters/11052257)  
**Lori's Request:** Can you do something with dark!Dean? Demon Dean or MOC Dean works too. I'd like more emphasis on how good Dean feels, how liberated he is with his new agenda, morals etc. Also, if you fit the theme of betrayal - how Sam didn't look for Dean while he was in Purgatory as the possible reason for Dean's anger- it would be perfect. So Dean stalks and claims his brother because unlike Sam, Dean needs his brother and now he's uninhibited enough to take what he always wanted. (If sex, only bottom Sam, pretty please)  
  
[**19\. I'm Here**](https://archiveofourown.org/works/4244124/chapters/11128661)  
**sixbucksandwingless' Request:** I would really love it if you wrote a fic with dom!Cas and sub!Dean, in canon verse. Dean comes home after a rough hunt and needs Cas to take him out of his head for a while. Cas uses his grace for bondage and whatever else you can think of. And please include lots of loving aftercare. Could you include begging, orgasm denial(maybe with a cock ring?), and spanking? You can still have Cas use his grace to tie Dean up with, or if you think it would work better using actual rope or handcuffs, that's okay too :)  
  
[**20\. Rough Ride**](https://archiveofourown.org/works/4244124/chapters/11421643)  
**Anon Request:** Can I ask for wincestiel fic where Sam and Cas wants distract Dean from the burden of the Mark and there no better way than some kinky sex...(sub-bottom!Sam, dom-top!Dean, anal), please?  
  
[**21\. Sub Drop**](https://archiveofourown.org/works/4244124/chapters/11544976)  
**Anon Request:** Before I was here I was reading a subdrop fic (there are not enough!) and I was like, omg, I must request that if I can bc it would be awesome in your hands. So yeah, I would love if Dean was suffering from pretty severe subdrop and needed to be taken care of. I like Dean/Sam for this type of scenario. Any other kinks are fine!  
  
[**22\. Swings Both Ways**](https://archiveofourown.org/works/4244124/chapters/11725649)  
**Anon Request:** For the ask box thing, since you write so wonderfully ❤️ could you do one where Dean comes out to Sam as bisexual, and he's afraid of what Sam might think, but Sam is okay with it. But later on Sam sees a group of men harassing dean about it, touching him and yelling at him, and Sam's anger explodes!! Super-protective Sammy please?  
  
[**23\. Five Times Sam Was Topped 2**](https://archiveofourown.org/works/4244124/chapters/11958026)  
**[Sandra's](https://archiveofourown.org/works/4463927/comments/38119871) Request:** Wonderful fic, I love when big man like Sam bottoming, this is so hot, I'd like see him fucked by Dean and Charlie any chance for sequel?”  
  
[**24\. Prosodic Stress**](https://archiveofourown.org/works/4244124/chapters/12254084)  
**This is soupernabturel and assbuttintheimpalafiction‘s fault:** [This Post](http://assbuttintheimpalafiction.tumblr.com/post/134153078728/soupernabturel-just-shower-thoughts-the) from Shower Thoughts read “The sentence “I never said he licked my asshole” has 7 different meanings depending on the stressed word.” So of course soupernabturel had to say “I need a Destiel fic showing all the different ways you can use this sentence, don’t ask me why I just do” and assbuttintheimpalafiction followed that up with #yessssss · I'll settle for any that have bottom!cas.  
  
[**25\. Caught You**](https://archiveofourown.org/works/4244124/chapters/12276089)  
**Radioactivegleek's Request:** I'm going to request a fic here since I don't have a tumblr. Can you do a fic where Sam catches Dean using a pacifier, and decides that he'll treat Dean like a baby since he's acting like one? That would be great, thank you.  
  
[**26\. Save Room for Pie**](https://archiveofourown.org/works/4244124/chapters/12287627) **  
****Anon Request:** For your tumblr ask box request i would love you forever if you wrote some chubby!Dean/Sam where Dean is more than a little chubby. Dean can either be really self conscious or just totally proud and unashamed. I'm picturing Dean gained all the weight while Sam was in Hell and so it's a surprise when Sam finds his way back to Dean! It's a little weird for Sam but he loves Dean any way he can get him.  
  
[**27\. A Good Bitch**](https://archiveofourown.org/works/4244124/chapters/12287891)  
**[Anon's Request:](http://mayalaen.tumblr.com/post/129447335829/hi-maya-i-have-a-request-just-watched-dog-dean)** Hi maya, I have a request. just watched dog Dean episode again, wanted dogdean and his caretaker sam? The spell Dean put himself never wears off. So he behaves more like a dog and Sam should watch over him not to sniffing around:) Dean rather whining or barking than talking. Sam should help him wearing clothes, bathing, lacing up his boots, using tools. He even goes to rut, humping over sam's thigh when theyre sleeping, Sam fucks him like a bitch.(bottomdean please!):D Thanks for awesome works!  
  
[**28\. Show Me**](https://archiveofourown.org/works/4244124/chapters/12292361)  
**[jsquaredfever's Request:](http://mayalaen.tumblr.com/post/132075936769/im-currently-reading-your-tumblr-ask-box-requests)** Im currently reading your Tumblr Ask Box Requests on AO3 and have a request for you. Could you do a Sam Winchesterl/Castiel explicit story involving oral sex hard anal sex and lots of water sports please? Thankyou x Yeah, top Sam/ bottom Casiel please x  
  
[**29\. Holding On**](https://archiveofourown.org/works/4244124/chapters/13083502)  
**This** is my first reader insert fic. I was asked by an anon to write a Boyking!Sam x Reader fic and this is what my brain decided to write, but since I have no clue who the anon is and they never asked for Wincestiel, I wrote a second one (which will be in the next chapter), but that means this one is inspired by that request and not really a fill for it.  
  
[**30\. Good Job**](https://archiveofourown.org/works/4244124/chapters/13083613)  
**Anon Request:** Would you ever consider writing boyking!sam x reader? I wasn't looking for anything in particular I just thought it was an interesting concept and figured it would give you room to run and mold  
  
[**31\. Switching**](https://archiveofourown.org/works/4244124/chapters/13087378)  
**Anon Request:** I would love to read a story about J2 or Sam/Dean, both are strong characters, no D/s but pure s/m scene/relationship, all consensual, for pleasure of both. Figging, canes, belt spanking/whipping.  
  
[**32\. The Name Game**](https://archiveofourown.org/works/4244124/chapters/13089280)  
**Anon Request:** Could you do a mpregDean with Sam? Dean is nine months pregnant and Sam enjoys talking to their unborn daughter and feeling her move.  
  
[**33\. Never Gone**](https://archiveofourown.org/works/4244124/chapters/13277227)  
**Anon Request:** I was thinking Wincest with demon!Dean (doesn't have to be MOC version) still being super protective of Sam? Maybe after a hunt where Dean rescued him and Sam could tell how much Dean cared, Sam decides it's time to try sleeping together again? At some point during the sex Dean gets carried away and is too rough with Sam and almost hurts him and he's horrified but Sam understands and coaxes him through it?  
  
[**34\. Before**](https://archiveofourown.org/works/4244124/chapters/13277260)  
**Anon Request:** For the Tumblr Ask Box requests I saw on AO3, maybe Cas likes Dean to be real clean before their more intense/longer scenes so makes sure to shower/shave him etc beforehand, and he's all gentle about it, sort of like aftercare but beforehand and likes to include an enema or two just to make sure Dean is squeaky clean before their scene?  
  
[**35\. Longing**](https://archiveofourown.org/works/4244124/chapters/13277317)  
**Anon Request:** If you ever find yourself not busy with requests, might I impose? I would love to see some crobby mpreg with pregnant bobby. Perhaps Crowley makes a deal with him in Hell that he can have free reign, if he'll bear Crowley's children? But it's consensual on Bobby's part.  
  
[**36\. Bottles and Baths**](https://archiveofourown.org/works/4244124/chapters/13277407)  
**Anon Request:** Can you please write a non-sexual infantilism of baby!sam, daddy!dean and daddy!cas please?  
  
[**37\. The One Where You Do That Thing**](https://archiveofourown.org/works/4244124/chapters/13304551)  
**[Assbuttintheimpala's Request](https://archiveofourown.org/works/4244124/comments/38633255):** Could you do marine!Dean who has been deployed overseas for a while and he surprises his boyfriend twink!castiel with a visit. Rough, needy welcome home sex would be amaze Bottom!Cas too please with any other kinks you like :) Thanks heaps!  
  
[**38\. The Sniffles**](https://archiveofourown.org/works/4244124/chapters/13305946)  
**[Anon Request](https://archiveofourown.org/works/4244124/comments/40491367):** I have a kink for sneezing/illness/caretaking. I would like something with Sam/Dean where Sam gets off on Dean's sneezes. Or, honestly I would SERIOUSLY be just as happy with Sam getting off on just Dean being sick, minus the sneezing. Just like kitten-weak sick Dean and Sam... taking care of him. Sam should want to make him feel better but you can have him tease Dean or go a bit dubcon if you want with it too since Dean would be sick/kind of out of it, just no completely evil!Sam please.  
  
[**39\. A Lasting Impression**](https://archiveofourown.org/works/4244124/chapters/13404697)  
**Anon Request:** Can you write a one-shot where Dean spanks a human, ex-angel canon Cas? Its long and merciless and A long time coming, until it's over--then it's all comfort and fluff. No sex.  
  
[**40\. Do You Want to Come?**](https://archiveofourown.org/works/4244124/chapters/13859380)  
**Rieraclaelin's Request:** May I ask for a prompt? I know you have a lot more ahead of mine, but, if you feel like doing it, I would be totally ok with it! ;) (and if you've already done one like it, just ignore it!) May I have a Sastiel d/s type prompt, with a lot of Cas edging Sam with any kinds of toys, as well as possibly some grace kink! type edging? Basically until Sam is nothing but a whimpering, incoherent mess before Cas lets him come? Also, I wouldn't object to any spanking and panties!  



	2. Open Your Eyes

**Summary for the Chapter:**

> Anon Request: Cas fingering Dean while Sam’s sleeping in the next bed. Dirty talk, D/s, aggressive Cas.

**Notes for the Chapter:**

>  **Warning:** Cas teases Dean about Sam waking up while they're fooling around, but there's no Sam/Dean interaction.
> 
>  **Tags for This Chapter:** D/s, fingerfucking, anal fingering, prostate massage/prostate milking, dirty talk, roleplay, fantasy talk about incest (but no actual incest)

“Shhh,” Cas hisses in his ear as his right hand wraps tighter around Dean’s mouth.

Dean is trying to keep calm, but there’s two fingers shoved in his ass, playing with his prostate, and his little brother is asleep in the bed not even three feet away.

“If Sam wakes up, he’s going to see you squirming,” Cas warns.

Dean squeezes his eyes shut. He doesn’t want to see Sam sleeping, doesn’t want to know if he moves or starts breathing differently. Dean has slept in the same room with Sam most of their lives, and he knows exactly what sounds and movements mean Sam’s about to wake up. If he sees that, he doesn’t know what he’ll do.

“Open your eyes and look at him,” Cas says, a whisper that tickles his ear.

Dean lets out a squeak as Cas pushes hard on his prostate and drags his fingers down and out before shoving them right back in.

“Watch his breathing,” Cas says.

Fingers are rubbing over Dean’s prostate, pressure so intense Dean’s worried he’s going to piss himself.

“What if he wakes up?” Cas says, stroking and stroking, pace too fast to get even a moment’s rest. "What if he sees you like this? Tears running down your face, eyes wide, fingers almost ripping the sheets as you pull and squeeze.“

Dean is panting through his nose, sure he’s going to pass out long before he comes. And that’s if Cas lets him come.

"Would he be shocked?” Cas asks, his left leg wrapped securely over Dean’s legs, keeping him right where he wants him. "Would he think it was hot? Seeing you like this, desperate to come on just my fingers?“

Dean wants to just grab his cock and get himself off, but he knows better. Cas told him not to, and Dean is well aware of the consequences for disobeying a direct order like that.

"Maybe he’d sit on the edge of his bed,” Cas continues, “stroking himself as he watches every single move you make, every shiver, every flinch.”

And Dean does flinch. Cas knows exactly how to play with him, and the pressure inside him is becoming unbearable.

“Your cock is mine just as much as the rest of you is,” Cas says. "That means I can let Sam watch if I want to. I could wake him up right now and he’d thank me for the privilege of watching you come apart.“

Dean sees the hitch in Sam’s breathing. Sam isn’t waking up, but he’s probably going to move, and sure enough he does, turning on his side, facing Dean.

"I’m not even going to let you come,” Cas says. "I’m going to milk you, make it dribble out of you, and you’ll be a mess of nerves and drenched in sweat once I’m done with you.“

Dean whimpers as Cas pushes down even harder. And that’s the last straw. He feels his stomach clench and something between his stomach and cock yanks tight before a wave-like feeling starts to radiate from the center of his body outward. He wonders if it’ll ever stop or if he’ll be stuck like this for the rest of time. It’s coming from deep inside him, not his cock, not really his stomach, and he feels something dribbling out of his cock as his hips thrust forward.

He’s sobbing, body stiff as a board, eyes locked on Sam as he prays his little brother doesn’t wake up. When it’s over, he feels as if he’s been chased through the woods for hours by a creature that was only a few feet behind him. He’s drained and feels almost cold, but warm at the same time. He’s numb, but oversensitive. He’s satisfied, but not in a way he normally feels when he’s had a really good orgasm.

When Cas pulls his fingers out of Dean’s ass, Dean lets out another sob, but soon Cas is rolling him onto his back and kissing his cheek, his forehead, and that little spot just under his jaw on the left side that makes him squirm with pleasure.

"Sleep,” Cas says.

Dean obeys, just like he does every other direct order Cas gives him.


	3. Tips to Make Your Girl Weak in the Knees

**Summary for the Chapter:**

> Anon Request: Dean/Cas -- kill me with adorable and fluff. Cas wants to date Dean. He reads about how to woo someone in a magazine.

**Notes for the Chapter:**

>  **Warnings:** No warnings for this chapter other than swearing.
> 
>  **Tags:** Fluff, cuteness, romantic gestures.

"Here," Cas says, thrusting a daisy in Dean's face.

Dean's eyes cross as he takes the tiny flower from Cas, but by the time he looks up, Cas is gone. Dean turns to Sam, but Sam just shrugs and drops their duffels on the motel room beds.

"I'm hungry," Sam says. "Want anything?"

"Yeah, gimme a couple burgers from the place next door," Dean says as he sets the daisy down on the dresser.

"'K, be back in a few minutes," Sam says, leaving Dean alone in the motel room with his little daisy.

*

Dean frowns as he picks up the piece of paper that had been shoved into his boot. He hadn't noticed it until he'd already had his foot in there, and after his totally unreasonable freakout over the possibility of a gigantic spider being in his boot, he reads the note.

_Thinking of you! XOXO_

Dean opens his mouth, ready to ask what the fuck is going on, who the fuck put this in his boot, but he's alone in the motel room. It's not Sam's handwriting, as if Sam would ever write a note like that, but he can't rule out the possibility of the cleaning woman slipping it in.

He goes to the window and pulls the curtain aside, looking for said cleaning woman. She's heading for the office, her cart creaking as she pushes it.

"Nah," he says, shaking his head. It had been a silly thought.

*

"Oh, shit," Dean hisses as the pair of lacy panties tumble to the floor of the laundromat. "Shit, shit, shit."

He's a guy in his thirties, washing his slime-encrusted clothes in the middle of the night. If anyone sees the panties, they might just call the police. Yeah, he really does look that bad with the ripped jeans, blood-stained T-shirt, and smelly jacket. Not to mention his hair still has leaves and twigs in it even though he ran his hands over his head a couple times.

Dean grabs the panties and shoves them in his pocket so hard he hears the stitching of the pocket rip just a little. He didn't recognize the panties. Not from any of the girls he's been with lately and his own are well-hidden in a compartment deep within the trunk of the Impala.

He heads for the restroom, locks himself in the stall, and pulls out the panties. They're actually really cute, and they're so soft that he can't wait to try them on. He feels his face flush when he realizes they're his size.

Dean raises the panties to his face and sniffs, but other than that new clothing smell, there's nothing else. He runs his thumb over the little pink bow, which really finishes the satiny light pink material they're made of. He has no idea how they ended up in his duffel bag with his other dirty clothes, and he really hopes it wasn't Sam.

"Fuck," Dean says, closing his eyes and smacking his forehead on the stall door.

What if Sam found the compartment in his trunk? What if Sam had bought these and the moment he stepped back into the motel room, Sam was going to let loose with all the mocking he could muster?

Dean's sweating by the time he gets back to the motel, but Sam just grunts a 'hey' as greeting. Dean doesn't know if he's relieved or even more freaked out that it wasn't Sam.

*

"...and we need to-ah!" Dean yells as Cas appears in front of him. He nearly runs the angel over, but manages to stop in time.

Sam's snickering next to him, but at least no one else is shopping at Save-Mart this late at night, so probably no one noticed Cas appearing out of thin air.

"This is for you," Cas says, holding a pie in his hands, which he shoves toward Dean.

Dean's eyes widen. He has no idea how to react. Sure, he's happy about the pie, but what the fuck. "Um, thanks, Cas," Dean says, taking the pie from Cas. "But what... fuck," he swears, because Cas is already gone.

He turns to Sam, holding the pie out at him like Sam can give him an explanation or maybe tell him that he just hallucinated the whole thing.

But Sam, the idiot, is just grinning. That stupid grin he gets sometimes when Dean is being a dork. Dean lets out a frustrated sigh and takes off down the aisle, searching for the bags of salt.

Later, when they're standing at the cash register, Sam drops a bag of plastic forks onto the conveyor belt, smirking at Dean as he says, "For your pie."

Dean thinks he hates Sam a little bit.

*

"Ow," Dean says as he spreads out on the bed, face down.

"You want some pain meds?" Sam asks from the bathroom, having just started the water in the shower.

"No, I'll be okay if I just don't move for a while," Dean says.

He's glad he was able to drop his jacket before he belly flopped, but he wishes he would've done the same with his jeans and boots.

"I said I'm okay, Sam," Dean grumbles as a weight settles on the backs of his thighs, but then he's groaning as not-Sam's-hands start massaging him. "Okay, I changed my mind. Just keep doing that for about the next ten or twenty years."

"Try to relax," Cas says, hands strong and sure as they find every knot and work them out.

Dean falls asleep before Cas is done.

*

Sam walks into the back of him when Dean stops cold in the doorway of the latest shitty motel room they're staying in.

"What's wrong?" Sam asks, already gearing himself up for a fight.

"Who knows this was our room?" Dean asks, slowly approaching the bed near the door.

"Us," Sam says, and Dean can hear the frown in his tone of voice. "Oh, and I told Cas we'd be here."

Dean eyes the red box with a beautiful white bow resting in the middle of the bed. There's a tag attached to the bow, so Dean carefully turns it over.

"For Dean, from Cas," Dean reads, squinting at the little smiley face and tiny hearts that had been drawn on the tag. "What the fuck?" he says, turning to Sam.

But Sam, the asshole, is laughing. He's laughing so hard his shoulders are shaking and he's bending over at the middle.

"What's so funny?" Dean asks. "You think this is funny?"

"No," Sam says, standing up and holding his stomach. "It's the two of you. You're so fuckin' adorable that I can't stand it."

"What are you talking about?" Dean asks, getting a little defensive for reasons he can't quite pinpoint.

"Ask Cas," Sam says, shaking his head as he starts heading back out the door.

"Wait!" Dean says. "Where the Hell are you going now? Tell me what the fuck is so funny!"

"I'm getting my own room," Sam says, from the doorway, one hand on the doorknob. "Call Cas and ask him. Make him answer you, and I'll see the two of you tomorrow morning for breakfast."

"Hey!" Dean yells, but it's too late. The door is closed and Sam's gone. Dean sighs. "Okay, we're gonna play it this way. Cas? Castiel? Can you get your ass down here right now and-ah!" he says, flinching when suddenly Cas is standing in front of him.

"Yes, Dean?" Cas asks.

Dean tries to ignore the slightly hopeful expression on Cas' face. "What the fuck is this?" he asks, pointing at the box on his bed.

Cas' face falls, hurt expression taking over, and Dean feels like an asshole for doing that to him, but he has no idea why it upset Cas so much.

"You don't like it?" Cas asks, wounded eyes stabbing Dean in the chest.

"No, I mean yes," Dean says, then shakes his head. "Wait, no. I didn't open it yet. I'm asking why it's there in the first place. And because Sam seems to find this funny, I wanna know if this has anything to do with the other gifts you've given me lately."

Cas blushes. He fucking blushes. Dean didn't even know angels could blush, and it makes Dean wonder if the vessel had the physical reaction because Cas wasn't really paying attention or if Cas was getting better at faking the human thing.

Instead of answering, Cas opens the box, reaching around Dean. Dean peers inside, unable to stop himself, and he forgets to breathe for just a moment because there's a cassette tape, a teddy bear holding a heart, a box of chocolates, and a single rose in the box.

Suddenly the look on Sam's face, all the girly giggling, and getting a separate room for the night makes sense.

Cas takes Dean by the hand, an awkward little smile on his face. "May I take you to dinner?" he asks.

Dean's sure his mouth is hanging open and equally as sure that he looks really fucking stupid, but he can't believe this is happening. An angel just asked him out to dinner. After giving him gifts and courting him like he's a pimply and nervous teenager.

"So, ah, the gifts?" Dean says, unsure what he's really trying to ask.

"The magazine I read suggested each of those gifts before asking your intended out for dinner," Cas says.

"What magazine?" Dean asks, because really he can't make his brain accept all the other shit going on inside it, and the magazine is a good thing to focus on.

"Something called Cosmo," Cas says, then frowns. "Did I do it wrong? The woman at the convenience store assured me it would work."

And that's it. Dean has no response, no defenses for what has just happened. He's never been courted before. And Cas is standing there, earnest expression on his face, hope in his eyes, and his hand feels so warm in Dean's.

The trouble Cas went to, well, it's humbling and pretty much the sweetest thing he's ever seen.

"No, Cas," Dean says, shaking his head. "You did it right."

Cas' smile melts Dean's heart. At least what was left of it. He thinks it may never recover.

"The panties were from you?" Dean asks.

Cas nods. "Yes, Charlene said you'd want to know I find you sexy."

Dean can't laugh at Cas, he really can't. It's so fucking sweet, and knowing that Cas took advice from a gas station cashier makes something in his gut clench, because no one's ever done something like this for him before.

"Yes," Dean says. "I'd love to go to dinner with you."

Cas smiles again. "I'll pick you up tomorrow night at seven p.m."

"Okay," Dean says, his cheeks hurting because of the gigantic smile on his face.

"I'll see you then," Cas says, and then he's gone.

Dean stands there for a moment, still in shock, but then he turns to the box and pulls out the gifts. He's got a box full of chocolate and Sam's gone for the night, which means it's all his.

It also means Sam won't see him leaving the rose and teddy bear on the nightstand next to his bed that night.


	4. Size Doesn't Matter

**Summary for the Chapter:**

> Assbuttintheimpala's Request: Twink!cas (maybe senior in high school) having a secret relationship with cop!dean (who's maybe like 30) and Cas is a total size!queen so he asks Dean to fuck him with both his cock and his night stick? If you could put in some humiliation/slurs like Dean telling Cas how much of a slut he is and commenting on his gape that would be awesome. Also maybe for the scene they're somewhere they could easily be caught? Maybe Dean had sneaked into Cas' bedroom in the middle of the night?

**Notes for the Chapter:**

>  **Warnings:** Twink!Cas (he's 18) and cop!Dean (he's 30) fucking on school grounds. Object insertion (nightstick) and humiliation/slurs and dirty talk.
> 
>  **Tags:** Consensual sex, object insertion, daddy kink, age kink, humiliation and slurs, dirty talk, anal sex, rough sex, felching, gaping, manhandling

"How the fuck did you get in here?" Dean hissed as he pulled the kid into one of the bathroom stalls. "If they see the two of us in here, I could lose my fucking job!"

Cas grinned at him as he plastered himself against Dean's front. "I'll just tell them you're my daddy," he said, batting his eyelashes even as he grabbed Dean's crotch.

"Fuck," Dean breathed, head thunking back against the stall door.

"Besides, I'm eighteen," Cas said before pulling Dean's nightstick out of it holster. "You can fuck me without getting in trouble."

"I'll still get in trouble," Dean said. "We're in the middle of the school grounds. That's conduct unbecoming. Not to mention the school would sue me."

"Then I'll just be really quiet," Cas said, then stood on his tip toes so he could whisper in Dean's left ear, "Daddy."

Dean shivered. "Such a fuckin' slut," he said under his breath.

"Just for you," Cas said as he worked Dean's belt and slacks open. "I'm all ready for you. You can just bend me over and fuck me. I'm all wet and aching for you, Daddy."

"Okay, knock off the daddy shit," Dean said, wincing as he looked down at Cas. "I already feel like a dirty old... fuck," he trailed off as Cas wrapped his lips around the end of Dean's nightstick and sucked.

Cas looked him in the eye, a challenge as he hollowed his cheeks, sucking on the nightstick like it was a cock, really putting on a show. He pulled the nightstick out of his mouth and held it up between them. "Maybe you should stretch me with this before you put your big cock inside me," he said, somehow all the while looking innocent.

"You scared of my big cock, baby?" Dean asked, grinning.

"It's really big," Cas said, eyes widening as he nodded. "It hurts."

"Aww," Dean drawled. "It hurts when I stretch that slutty little hole with my cock?"

"Uh-huh," Cas said, then turned around and straddled the toilet, putting his hands on the wall and shoving his ass back at Dean. "It's so big!"

Dean groaned as he realized Cas had already dropped his jeans and panties, having stepped out of them, bare feet on the dirty bathroom floor.

"Such a dirty little boy," Dean said as he shoved two fingers into Cas' hole, hissing when he found it wet and already open for him. "You're not tight at all, you little slut," he scoffed.

"But you're so big," Cas said, pouting over his shoulder. "It still hurts."

Dean smirked, knowing full well Cas didn't even consider letting anything less than above average inside his hole. The bigger the better. "Then I guess I'd better open you up even more."

Cas whimpered as Dean slowly pushed the nightstick inside Cas' hole, inching it in before pulling out, only to push in again.

"Keep your mouth shut," Dean ordered. "If you get loud, I'll stop."

"Yes, sir," Cas said, wiggling his ass enticingly.

Dean wrapped his left hand around Cas' left hip, holding him in place while he fucked Cas loose hole with his nightstick, the squelching noise only making him harder.

He pulled the stick out and tapped it on Cas' rim. "Look at that hole. Such a cockslut that I bet it never gets tight."

Cas pushed his ass back, letting out a little whimper. "I'm all empty. I need you inside me. Want that big cock inside me, Dean. Please! Want it filling me up!"

"Shh, keep it down," Dean said, slapping his cock down on Cas' left ass cheek. "You don't get my cock unless you're a good boy."

"Sorry," Cas said, pouting again. "I'll be good."

Dean pushed into Cas, going balls deep without giving Cas a chance to adjust. Cas hissed, going up on his toes, but he didn't pull away. Instead he pushed back, wanting more.

"Fuck me," Cas said. "C'mon, fuck me."

Dean chuckled, then wrapped his arms around Cas, pulling him back against him and holding the nightstick to Cas' mouth.

"Suck," Dean said.

Cas shivered, obeying immediately, and Dean nearly breathed a sigh of relief. Shoving something into Cas' mouth usually shut him the fuck up. He needed this job.

Dean took hold of Cas' cock with his right hand as he fucked him, giving the kid some stimulation. He really didn't need to. Cas loved being fucked, especially when the cock was a big one, and he could come on that alone. But Dean liked the feeling of a small cock in his hand.

Cas' cock was nothing to laugh at, but it wasn't nearly as thick or long as Dean's. And when Dean squeezed it harshly, Cas clenched around him, whimpering around the nightstick in his mouth.

"That's a good boy," Dean panted in Cas' ear. "Take that big cock, you little slut. My little bitch."

Cas reached up and grabbed Dean's hair, holding him close in a silent demand for more dirty talk. Dean chuckled, nibbling on Cas' ear.

"You like being my little bitch?" Dean asked, grinning when Cas nodded, choking on the nightstick as Dean pushed it in a little too far. "Yeah, you love it when I split you open. I bet you'd look pretty in my bed, all fucked out and leaking my come outta that sloppy hole."

Cas squeaked as Dean squeezed his cock again. The kid was about to come, and Dean didn't think he'd last much longer himself, so he fucked him faster, lifting Cas off his feet as he thrust into the smaller body in front of him.

"Gonna fuck you so hard," Dean whispered, "you'll be feelin' me for a week. You'll be walkin' funny, and everybody's gonna know it's because somebody fucked you real good. Somebody broke that hole and left you sloppy and leaking. And they'll all wanna know who it was that fucked you. Who had such a big cock that it filled up that busted hole."

Cas moaned around the nightstick, his hole clenching around Dean's cock as he came, his jizz hitting the toilet and wall in front of them and dribbling down. Cas went loose around him, even more than before.

"Oh, that fuckin' loose hole," Dean groaned. "I ruined it. You feel that? I ruined that sloppy hole."

Cas gagged again on the nightstick as Dean thrust forward hard, coming deep inside Cas. He heard Cas grunting, felt him squirming as he tried to get his feet firmly on the floor again.

"Oh, fuck yeah," Cas sighed as Dean pulled out and dropped to his knees behind Cas.

"You're leakin' all over," Dean said, smirking. "Look at that. You couldn't even hold it in if you wanted to, you little slut."

Cas moaned, his thighs shaking as Dean licked him clean with broad swipes of his tongue over Cas' hole. By the time Dean stood up again, Cas let himself crumple down onto the toilet, his forehead on the tank and his legs spread wide around the bowl.

Dean pulled his own boxers and slacks up and fixed his uniform. "Clean yourself up," he said, smirking as he walked out of the stall.

"Fucker," Cas grumbled.

Dean chuckled as he threw the restroom door open and started his rounds, Cas' dried spit still on the end of his nightstick.


	5. Do As I Say

**Summary for the Chapter:**

> **Curlysupergirl's Request:** Can you write a chapter about Dean with complete loss of control (maybe TPE) with Cas in charge? Like the first prompt with humiliation, but maybe this time Sam actually witnesses it (doesn't necessarily need to be sex).

**Notes for the Chapter:**

>  **Warnings:** Nothing extreme and there’s no actual sex. Some swearing.
> 
>  **Tags for This Chapter:** Dean/Castiel, D/s and TPE, crossdressing.
> 
>  **A/N:** This didn't turn out how I thought it was going to when I first started, but I hope you like it :)
> 
> Because of their lifestyle, I went with an alternate version of TPE that works for a lot of people in M/s relationships where the slaves still have jobs of their own and the Master doesn't micromanage.

"Yeah, I'd like a burger and...," Dean started, but then he glanced at Cas. "The meatloaf dinner. I'll have that," he said, flashing a smile at the waitress.

Sam frowned. What the fuck was that? He couldn't remember the last time Dean ordered anything but a burger, fries, and a slice of pie at a diner. He decided not to say anything. It was odd, but Cas had mentioned just a few days ago that Dean was eating too many greasy burgers.

"Meatloaf sounds like a good choice," Cas said. "I'll have that too."

Sam could maybe have dismissed Dean's food order as just a small effort to keep Cas off his back about his health, but the way Dean's face flushed, the way he ducked his head when Cas said the meatloaf was a good choice? That he couldn't ignore.

It was fucking adorable. Sam knew Cas had Dean wrapped around his little finger, but it was great to see Dean getting approval in a relationship. His brother deserved some praise.

*

"It's fuckin' hot," Sam said, holding a bottle of water out to Dean as they trudged through swamp lands in the middle of summer.

"No, I don't need...," Dean started, but when Cas cleared his throat, he took the bottle of water from Sam. "Thanks," he said.

Sam usually had to fight back and forth with Dean for a few minutes before Dean would stop halfway through a hunt to get a drink of water.

Dean still threw the empty water bottle at Sam's head, so all was apparently good.

*

Sam scrunched his nose up. "So tell me again why you're not going to take your knife with you on this hunt?"

Dean shifted from one foot to the other while he shoved his gun into the back of his jeans. "Because I don't want to."

"But why? You always take it," Sam said.

Dean sighed, turning to scowl at Sam. "Because I left it on the floor in the back seat instead of putting it away, and so I probably shouldn't use it for a while until I appreciate it enough to take care of it."

Sam stood there for a moment, staring at Dean while his brother closed the trunk and took off toward the abandoned building, Cas close behind.

"What the fuck?" Sam said under his breath, then shook his head and followed them.

*

"What are you wearing?" Sam asked, trying to keep a straight face.

Dean stood up so fast he almost fell over. His face was flushed, but then he just smirked. "Cas wanted me to wear 'em under my jeans," he said, pulling his T-shirt down so the pink lace didn't show over the top of his belt.

Sam chuckled. "You better hope you don't get arrested with those on."

Dean rolled his eyes. "Do I look like the type of guy who would lose if I went up against a bigoted police officer?"

Sam shook his head. "Nope. But I'm never gonna let you live it down if you're sitting in a jail cell wearing pink panties under your jeans."

"Oh, ha-ha," Dean sneered, then shoved by Sam as he walked out of the motel room.

*

Dean was squirming in the driver's seat, but they had passed by three rest stops, and Dean still wasn't pulling off the highway.

Sam rolled his eyes. His brother could be so stubborn. "I gotta pee. Can you stop at the next exit?"

Dean nodded, but instead of looking relieved, he met Cas' eyes in the rear view mirror, wincing and squirming again. Sam had no idea what was going on, but for all he knew there was a plug up Dean's ass. He didn't want to know.

Sam got out, but when Dean didn't follow, he leaned back down into the car, holding the door open. "You comin?" he asked Dean.

Dean shook his head. "I'm fine," he said, obviously lying.

"Don't hurt yourself," Cas said from the back seat, voice low.

"Just go take a piss," Dean said, waving Sam off.

"Dude, you look like you're gonna piss yourself," Sam said. "Come with me."

"No, I'm fine," Dean said, but the nonchalance was gone. He was clearly upset.

Sam looked to Cas, a horrible thought making his protective instincts suddenly flare. "Did you tell him he couldn't go?" he asked Cas.

Cas shook his head. "No."

Sam turned to Dean again. "You're gonna hurt yourself. Just come with me." He wouldn't have normally been pushing it, but Dean was beginning to sweat, eyes wide and desperate.

Cas leaned forward and whispered in Dean's left ear. Sam couldn't hear what he was saying, but Dean's shoulders slumped before Cas leaned back.

"I don't want to," Dean said, teeth clenched.

"Dude, what the fuck is going on?" Sam asked, the whole thing so bizarre that he was getting the creeps.

Cas opened his door, and in a move faster than Sam thought possible, Dean was out of the car and walking to the restrooms before Cas had even stood up.

"I'm going, I'm going," Dean said.

Sam watched as Cas casually followed Dean, but instead of letting them have their privacy, Sam went in after them.

"...don't want to sit," Dean hissed, then turned to Sam, eyes widening and his jaw dropping when he realized his brother had heard that last bit.

"You're going to hurt yourself," Cas said.

Dean scowled at Cas. "Then don't insist I...," he started, then his face flushed.

"Okay," Sam said, holding his hands out, "if you guys are doing some sort of sex thing, then just let me say that you really shouldn't fuck around with your bladder. It _can_ explode."

"Shut up, Sam," Dean said, not even able to look at him.

"That's all I'm gonna say," Sam said, then headed for a urinal.

"All you have to do is say the word," Cas said, voice soft, but not too soft for Sam to hear.

And Sam knew it had been for his benefit, because soon Dean was sputtering and pacing.

"No! I don't want to do that!" Dean said. "I just don't want to do this either."

Sam felt like smacking his forehead against the tiles in front of him. His brother could be so fucking stubborn.

"It's one or the other," Cas said, keeping his calm.

"Fine!" Dean yelled, startling Sam. "You want me to sit on the fucking toilet and piss like a fucking girl! I'll do it. You get your way. Hope you're happy."

Sam really wished he hadn't had a full bladder. It seemed as if he was never going to be finished pissing. He heard Dean slam the stall door closed and throw the lock as if it was the reason he was being made to do something that was so humiliating for him.

Finally Sam finished, washed his hands, and headed out to the car. Cas was already sitting in the back seat, and Sam sighed, really not looking forward to the awkward silence.

And it was taking forever for Dean to come out of the restroom. Sam wondered just how long Dean had held it if it was taking so long.

"Your brother is stubborn," Cas aid.

Sam cringed. "Yeah, he is."

"I don't mean him harm," Cas said.

Sam nodded. "I know."

"He could've gone at any time," Cas said.

Sam wished for the zombie apocalypse to start. Anything to stop this conversation. "I know."

"He needs it," Cas said.

"Needs what?" Sam asked, his mouth making the decision long before his brain caught up, and when it did, Sam wanted to kick himself.

"To have boundaries," Cas said. "He needs to know someone is watching out for him. That someone cares about him. He doesn't like everything I order him to do, but overall he likes being praised when he obeys, even in small things."

The zombie apocalypse wasn't coming, and no planes had crashed, no creatures had stumbled out from behind the bushes to assault him. He was stuck with Cas, and the awkward was so thick he felt like he could cut it with a knife.

"It's between the two of you," Sam said.

"But you love him," Cas said. "You're his brother and you care about him. He didn't want you to know what was happening, but the two of you are too close. You're bound to see some of it, and I don't want you to worry about me hurting him. Besides, he doesn't get to decide whether I tell you or not."

Sam closed his eyes and ran his hands over his face, his stomach clenching. But then he thought about it. He removed himself from the unease and really thought about what Cas had said.

"He's been smiling," Sam said, as if it was a revelation. Because it was. "I've noticed it for a while now. I thought he was just really happy to be in a relationship with you, but yeah, I've seen a change in him."

"I love him," Cas said. "And I'll do everything in my power to make sure he's as happy and content as he can be. That includes keeping you happy and content."

Sam chuckled, shaking his head.

"That's why I decided to tell you," Cas continued. "It may embarrass Dean, but your worry and concern is upsetting him."

Sam winced. Yeah, that sounded like Dean. Just as he was about to say one more thing, Dean got back into the car. By the look on his face, Sam knew Dean had been psyching himself up to come back out. He was looking straight forward and his jaw was set, both hands on the steering wheel after starting the car.

"As long as you're happy," Sam said, "I don't have a problem with any of it."

Dean didn't say anything, but after a few miles of driving, his body slowly started to relax. A few hours later they pulled into the parking lot of a motel that looked decent but not too high-priced. Dean turned the car off, then turned to Sam.

"Get us separate rooms," he said, handing Sam his wallet.

"Dean, I-," he started.

"You might wanna ask for rooms at opposite ends of the motel," Dean said, smirking, "unless you wanna be up all night listening to your big brother getting laid."

Sam let out a bark of laughter before he eased himself out of the car and headed for the office.


	6. Run Trip and Fall Chapter 2

**Summary for the Chapter:**

> Anon Request: I didn't know that you take ask-box request! Can I request you too? About J2(Bottom!Jensen) having rough-sex and hyper-sensitivity with crying!Jensen. Jared is very animalistic but with after-caring schmoop:) I love your 'Run Trip and Fall' so much, It can be same verse with that (Especially mentioned fisting thing). Sorry about long request. Always thanks for amazing works!

I'm posting a notice here, but please go to [Chapter 2 of Run Trip and Fall](http://archiveofourown.org/works/3778069/chapters/9995438) to read this fill. It works as a standalone or you can read it as part of the RTaF 'verse.

I can't seem to find where the original request was posted (I think it was Tumblr), so I'm glad I copied it. Anyway, as anon requested, it fit so well into my Run Trip and Fall 'verse that I decided to add it as [Chapter 2 of Run Trip and Fall](http://archiveofourown.org/works/3778069/chapters/9995438), but it's an anon request fill from someone who read the 'verse and found out I did [Tumblr Ask Box Requests](http://mayalaen.tumblr.com/post/122749813129/ask-box-requests).

Enjoy :)


	7. Filled Up

**Summary for the Chapter:**

> **Anon Request:** Could you write a Dom Dean where he keeps Cas filled with piss and cum all the time, and when not filled, he keeps him stuffed with dildos and/or random object's, and Cas loves it. Maybe lots of dirty talk/humiliation?

**Notes for the Chapter:**

>  **Warnings:** No warnings for this chapter.
> 
>  **Tags for This Chapter:** Watersports/pissing inside someone, fucking/anal sex, begging, mild D/s, butt plugs/toys, dirty talk, humiliation, established relationship.

Dean's hips were still moving, a slow, unhurried slide in and out of Cas. Not too far out, not so much that his load would dribble out of Cas' used hole.

"Feel me inside there, Cas?" Dean asked, arms wrapped around Cas as he rubbed his nose and cheek over Cas' back and shoulders.

"Yeah," Cas moaned into the bed, the movie on the shitty motel room television completely forgotten.

They were both sweaty, sated, and thoroughly enjoying the fact that Sam had gotten his own room for the night. On the other side of the motel. Well out of earshot.

"Fillin' you up," Dean said, then sucked another hickey into Cas' neck. It would disappear quickly, but Dean still liked to see them there for a short period of time. His marks on Cas. His claim.

"Yeah," Cas said, voice deep and muffled by the blankets.

"Ready for me?" Dean asked, grinning as he rubbed his nose through Cas' hair.

"Please," Cas said, desperate and eager even though he'd already come three times in as many hours.

Dean let loose, filling Cas up with his piss, groaning as his hips kept moving, not so much fucking Cas anymore and instead just rolling and squirming over his body.

"Dean," Cas whimpered.

And damn, but if that wasn't the biggest turn-on Dean had ever experienced. Making an angel whimper was something he wanted to brag about. Maybe introduce himself to everyone he met as, "Hi, my name's Dean Winchester, and I make angels whimper."

"What should I plug you with tonight?" Dean asked, grinning when Cas gasped, hips bucking against the bed. "I'm gonna need a big plug because I've wrecked this hole."

Cas squeezed around him, holding everything in. "The pink one. It's big enough."

"You gonna wear it for me all night?" Dean asked.

"Uh-huh-oh-mmm," Cas moaned, nodding.

And yeah, Dean decided he wanted to add incoherent noises to his list of accomplishments in the bedroom when fucking an angel.

"Hold it in," Dean said as he pushed himself up, palms flat on the bed to either side of Cas' torso. "If you leak all over the bed, I'm gonna make you lick it up."

Cas whimpered again, but squeezed even harder. "Hurry," he said.

Dean didn't need to hurry. Cas could hold it as long as Dean asked him to. He could also "accidentally" lose some of it on the bed and mojo the mess away. Grace meant Cas could do whatever Dean asked. But it was even hotter when Cas acted as if he didn't need to use any of his powers to do what Dean wanted.

"Hang on," Dean warned, then slowly pulled out. "Such a good boy," he said, patting Cas' ass when not a drop spilled from his hole.

"Please hurry," Cas said, turning his head to watch as Dean crossed the room and pawed through the duffel bag full of toys.

"This one?" Dean asked, holding up the maroon plug.

"No, the pink one," Cas said, a little frustrated.

Dean smirked. He'd picked the wrong one on purpose. "This one?" he asked, holding up the purple one.

"Dean, please!" Cas whined.

Dean chuckled. "Can't hold it in, baby?" he asked, watching as Cas poked out his bottom lip, pouting at him.

Dean wondered if sometimes Cas held back so much with his grace that it really was just a human in bed with him. That maybe Cas was actually begging because he was trying with all his might to hold in Dean's piss and the three loads he'd emptied into Cas' hole before that.

"All right," Dean said, wrapping his fingers around the large pink butt plug and padding over to the bed. He climbed on and got between Cas' legs. "Keep it tight. Your hole's all sloppy, so I'm just gonna shove it in."

Cas turned, pushing his face into the blankets. Dean couldn't help but smile. After everything Cas had seen and done, he had no idea how a mere human teasing him about bodily functions and sex could make Cas hide his face, blush all the way to the tips of his ears, and go quiet and still.

Dean pushed the plug in, the flared end popping into place as Cas gasped and squirmed. "Beautiful," he said, leaning down and placing a kiss on Cas' left ass cheek.

"Oh!" Cas yelped as Dean tapped the end of the plug. "Dean!"

Dean chuckled, thumping the plug harder, enjoying the little wiggle Cas was doing to try and get away from the sensation. The plug was big enough that it was most likely pushing on his prostate, and the vibrations had to be intense.

Finally Dean gave Cas a break, flopping down on the bed next to him and running his fingers through Cas' tousled hair. Dean closed his eyes and relaxed against the bed, a little smile tugging at the corners of his mouth.

Dean liked to think that if Cas was a cat, he'd be purring, tail lazily flicking back and forth. And then he remembered that he'd seen a cat-tail butt plug online. Well, now he had to order it. He'd have it sent to the motel, overnight express. Maybe he'd see if he could find a headband with kitty ears on it too. He couldn't wait to see the blush on Cas' face when Dean took those items out.

"I'll take it out in the morning," Dean said, flipping the blanket over the both of them and cuddling up with Cas. "You can let it all out before I fill you back up again while we're taking a shower."

Cas moaned his agreement, then pushed his face closer to Dean's, nosing at his cheek before brushing kisses against his lips.

"Feel so full," Cas said.

Dean reached between them and pushed against Cas' belly, chuckling when Cas cried out. "Yeah, you _are_ full. You can keep it all in."

"Mmm-hmm," Cas replied, eyes closed as he tried to get even closer to Dean.


	8. Dinosaurs and Cough Syrup

**Summary for the Chapter:**

> I really wanna read something cute and fluffy with baby dean (infantilism) maybe even sick dean? I like either cas or sam as the 'daddy' but it can be someone else. I prefer non-sexual, as for the 'setting' I don't prefer one over another, although I did enjoy Mr. Kitty's New Friend :) I also like it when a bit of the Adultness shines through like deans aware of what's happening but he needs it ya know?

**Notes for the Chapter:**

>  **Warning:** No warnings. There is nothing sexual about this.
> 
>  **Tags for This Chapter:** Infantilism/adult baby Dean, cold/fever/sick Dean, diapers, cough syrup, pouting and moody Dean, caretaker Sam.

"Daddy!"

Sam sat upright in bed so fast that he pulled a muscle in his stomach. "Ah, fuck," he hissed as he threw the blanket off, trying to stand up as quickly as possible so the cramp would quit, and also so he could get to Dean.

"Daddy!"

Sam winced as he hurried down the hallway, the panicked cries making him move faster. He walked into Dean's room and turned the lamp on next to the door -- the one that would only give the both of them enough light to see each other. The ceiling light would've been overkill.

"Daddy," Dean whimpered, sitting in his crib with a very forlorn expression on his face, red-rimmed eyes.

"What's wrong, little one?" Sam asked.

And that's when Dean let out a very wet-sounding cough and started to rub at his own chest as if it hurt. "Owie," he said, looking up at Sam with puppy eyes that put the master to shame.

Sam put a hand to Dean's forehead and sighed. "Are you sick, baby boy?"

"No," Dean said, frowning and shaking his head.

Sam chuckled, then lifted Dean out of the crib. "I think somebody's sick, but they don't like cold medicine."

"No," Dean said, wrapping his arms and legs around Sam, nearly squeezing the breath from Sam's lungs.

Sam walked into the master bathroom and set Dean down on the counter top. "Your nose is running, you have a fever, and you've got a cough."

"Uh-uh," Dean said, shaking his head, his diaper crinkling as he shifted on the counter, his T-shirt not nearly long enough to come to his legs.

"You're not coughing?" Sam asked, opening the medicine cabinet with his left hand while the other rested against Dean's waist to make sure Dean didn't make a run for it.

"Uh-uh," Dean said, then sniffed, a disgustingly wet sound. Dean gagged a little on the discharge most likely running down the back of his throat.

"Okay, I'll make a deal with you," Sam said as he set the bottle of cough syrup down on the counter. "If you can breathe all the way out and there's no coughing, then I'll just start the humidifier and give you some Tylenol."

Dean glanced at the evil bottle of cough syrup sitting next to him, then looked up at Sam, not so sure of himself. An expression of deep concentration came over Dean's face as he slowly blew out. Sam patted Dean's back when he started coughing.

"No!" Dean said as Sam unscrewed the cap on the bottle of syrup and suctioned out some of the nasty stuff with a large dropper.

"I'll make another deal with you," Sam said. Dean was pouting, but he seemed just a bit interested. "If you're a good boy for Daddy and get all of this down, I'll let you sleep in Daddy's bed tonight with me."

Sam forced himself to keep a straight face as Dean glanced back and forth between the evil bottle of syrup and Sam, carefully weighing his options. He loved sleeping with Daddy because he loved snuggling, but he really, really hated the cough syrup.

Dean finally came to a decision, shoulders dropping in defeat. "'K," he said, then opened his mouth for Sam.

"There's my good boy," Sam said as he squirted the liquid into Dean's mouth.

Dean swallowed, pulling a face that would've been more appropriate for a horrific accident or maybe the worst smell in the world.

"Open up again," Sam said, holding a cherry jelly bean up to Dean's mouth.

Dean surged up, grabbing onto the front of Sam's shirt as he happily took the jelly bean and started chewing. The cherry flavor and little bit of sugar helped to get rid of the icky taste. It was a trick Sam learned years ago.

"Better?" Sam asked, running the back of his fingers down Dean's right cheek.

"Yeah," Dean said, smiling.

If a jelly bean was all it took to get Dean smiling again when he was sick, then Sam was more than willing to keep a jar of jelly beans in his medicine cabinet.

"Daddy's bed?" Dean asked, trying to slide off the counter.

"Hang on a minute," Sam said, putting a hand on Dean's chest. "You're too warm."

And there it was. Adult Dean sat up a little straighter and for just a moment he opened his mouth, ready to tell Sam to fuck off, that he hated being wiped down, that Sam was an asshole for using freezing cold water on him, which Sam didn't do.

Sam stood a little taller and used his resolve face. He wasn't budging on this one, and if Dean broke character to throw a tantrum, Sam would win the argument in the end anyway because Dean tended to worsen quickly when he had a fever, spiking a temp, and even though Dean hated being wiped down, he knew that was the only way to bring the high temperature down.

Just like that, little Dean was sitting in front of him again. "No!" Dean said, then poked out his bottom lip.

Sam leaned forward and wrapped his arms around Dean, lifting him up. "C'mon, you know I won't use freezing cold water."

"S'cold!" Dean whined as Sam set him down on the king-sized bed before pulling Dean's shirt over his head and tossing it on the floor. "Cold!" Dean said again, wrapping his arms around his stomach and shivering as if to really get the message across to Sam.

"Don't move," Sam said. "Daddy's gonna get you a clean diaper, then I'm gonna wipe you down and read you a bedtime story."

Dean's pout eased up just a bit. "Die-sores?" he asked, a tiny grin lifting the corners of his mouth.

"All right, I'll read you Dinosaurs," Sam said.

Dean let out a small noise of victory that could've been a 'yes!' and the grin turned into a big smile.

"Stay there," Sam said, pointing at the bed.

"'K, Daddy," Dean said.

Sam walked to Dean's room first, grabbing a new diaper, the wipes, and some powder before he went back into the master bathroom and pulled a basin out of the cupboard, Dean watching carefully as Sam gathered everything. Sam filled the basin with room-temperature water and dropped a washcloth into the water.

Dean had scooted back on the bed, spreading out in the middle. Anyone else would've assumed Dean was being helpful. They didn't know Dean.

"No Dinosaur if you're gonna be a stinker," Sam said as he set the basin down on the nightstand.

Dean let out a sigh as he wriggled around until he was near the edge of the bed. "Cold," he said again.

"I know, but it'll get better," Sam said as he leaned down and pulled the tape from the diaper. He pulled the front flap down, then grabbed a wipe from the container and held it between his hands for a moment to warm it up.

Dean noticed Sam warming up the wipe and grinned. If Dean hadn't been wearing diapers and feeling awful because he was sick, then he would've teased Sam about doing something so adorable for him.

"Daddy's so mean, isn't he?" Sam asked, smirking. "Adding ice cubes to the water and using freezing cold wipes on you."

Dean spread his legs and let Sam clean him up, helpfully lifting his butt off the bed so Sam could slide a new diaper under him. Sam sprinkled a little powder on Dean's crotch before taping the new diaper in place, then dropping the used diaper on the floor next to the nightstand. He'd clean it up later. Right now he wanted to focus on Dean.

"You ready?" Sam asked as he took the washcloth and squeezed it over the basin, getting the excess water out.

"No," Dean said, but there was mischief in his eyes.

"Stinker," Sam said, then gave Dean's belly a bit of a poke.

"Hey!" Dean said, laughing as he squirmed on the bed, but then Sam was wiping him down, the awful, horrible, terrible washcloth not so bad now that Sam was taking such good care of him.

"You're gonna feel cold for a little while," Sam said as he made sure to wipe Dean's neck and under his arms, around his torso and down his legs, catching all the spots that held heat. "But it'll get better and you can help me read Dinosaur."

"Die-sore!" Dean said, smiling.

Sam chuckled as he finished with Dean's feet, getting between his toes, then tossing the washcloth back into the basin. He set the basin on the floor, then crawled into bed on the other side of Dean. The book was in the nightstand on the rarely-used side of the bed, so he opened the drawer and pulled it out.

Dean was still smiling when Sam got comfortable and held the book up so they both could see it, making sure he wasn't too close to Dean because he didn't want to transfer any heat to make the fever worse.

"How does a dinosaur say good night when Papa comes in to turn off the light?" Sam read.

"Daddy," Dean said firmly.

"Sorry," Sam said, hiding a smile. "How does a dinosaur say goodnight when _Daddy_ comes in to turn off the light?"

"Tail," Dean said, anticipating the next page.

"Does a dinosaur slam his tail and pout?" Sam read.

Dean pointed at the dinosaur's tail. "Die-sore's mad."

Sam turned the page. "Does he throw his teddy bear all about?"

"Teddy bear," Dean said, pointing at the stuffed bear on the page.

"What happens next?" Sam asked before turning the page.

"Stomp!" Dean said, then chuckled as Sam turned the page to reveal a dinosaur stomping its foot, throwing a tantrum.

"Does Dean do that when he doesn't wanna go to sleep in his own crib sometimes?" Sam asked.

"Daddy's bed," Dean said, turning to look at Sam, a grin on his face.

"Yeah, you like Daddy's bed," Sam said, nodding. "What does the dinosaur want?"

"'Nother story," Dean said.

Sam continued, "Does a dinosaur stomp his feet on the floor and shout: "I want to hear one book more"?"

"Book," Dean said, pointing out the book in the dinosaur's claws.

Sam could already tell that Dean's temperature was going down. Dean always seemed to be pulled toward him, as if they were magnets and Dean couldn't help himself, so even though Sam had tried to give him some room to cool down, Dean was almost up against Sam already. And there wasn't nearly as much heat radiating from him.

"What happens next?" Sam asked, getting ready to turn the page.

"ROAR!" Dean yelled, then laughed as Sam turned the page and let out a roar of his own.

"Does a dinosaur roar?" Sam asked.

"ROAR!" Dean yelled again, then coughed a bit, but his cough seemed a little better too.

"What's next?" Sam asked.

"Papa in a dress," Dean said, then laughed at his own joke.

Sam chuckled. It was the same joke every time, but Dean thought it was hilarious. Cas didn't get it at first, but then Dean had called him a silly Papa, and Cas agreed that yes, Papa probably was the Mama in the story.

"How does a dinosaur say good night when Papa comes in to turn off the light?" Sam read.

"Papa!" Dean said, pointing at the woman in a dress.

Sam snorted. Yeah, okay, so he still got a kick out of it himself. They finished the story, complete with lots of dinosaur roars and pointing out objects on the pages.

"Ready to go to sleep yet, little man?" Sam asked.

"Again!" Dean said.

Sam read it again.


	9. Customer Service with a Smile

**Summary for the Chapter:**

> Anon Request: AU or canon. Sabriel. Gabriel is a problem customer always complaining about something so he can spend time with Sam.

**Notes for the Chapter:**

>  **Warning:** None at all. Rated G and totally fluffy.
> 
>  **Tags for This Chapter:** Sam/Gabriel. This is just plain fluff, flirting, and cuteness. No sex. Not even any language.

"These are inedible!" the man said, frowning up at Sam as he thrust a bag of apples out at him.

"Oh, I'm sorry, sir," Sam said, smiling as he took the bag. "I'll get you a new bag."

Sam rolled his eyes as he walked into the back of the produce department. He didn't like the job, but he worked hard, and he needed the money. His scholarships paid for the college courses, but not the books or his food and housing. The job at the supermarket also meant he could take home damaged or past-due food. It was all still perfectly fine to eat, but they just couldn't sell it.

"I'm sorry for the inconvenience, sir," Sam said as he handed the new bag of apples to the guy.

"Thank you," he said, then looked down at Sam's name tag, "Sam."

"You're welcome," Sam said, flashing his charming smile.

"That kid at the front side the apples were fine," the man said. "But they were all bruised."

"Sorry about that," Sam said.

"I think I'll come to you from now on when I have a problem," the man said with a nod, then held up the bag of apples. "You pick out beautiful apples," he said, then turned and walked away.

Sam huffed out a laugh and shook his head. When he went into the back, ready to toss the bag of apples into the bin reserved for employees to take home and eat, he didn't see any bruising or damage at all. He rolled his eyes and put the bag back out front.

*

"They're stale," the man said, pulling a face that said only one taste of the horrid crackers had ruined his day.

"Sorry about that," Sam said, taking the box of crackers from the same man who had been very picky about apples only two days earlier. "I'll get you a fresh one out of the back."

Sam waited until the man had left with his new box of crackers before shoving a "stale" cracker into his mouth and munching on it. The crackers were fine. Sam sighed, chucking the opened box into the bin of take-home food.

*

Sam heard loud voices, the volume increasing, so he headed up front, frowning when he saw his picky customer waving a bag of bread in Ash's face.

"You might not be able to see it," the man said, "but there's mold! I smell mold!"

"I don't know what to tell you, sir," Ash said, and it sounded as if Ash was losing his cool, which never happened. "I've given you three different loaves of bread. Maybe I could interest you in another brand."

"It stinks of-oh!" the man said, smiling when he caught sight of Sam. "You! I'm sure you could help. This man over here can't seem to find me a loaf of bread that isn't moldy. Would you please find me one that isn't green and disgusting?"

Sam waved a flustered Ash away, then took the bread from the man. "Mr.?"

"Novak," the man said, "but you can call me Gabe."

"Gabe," Sam said, smiling, "I'll bring a new loaf of bread out for you right away."

"Thank you!" Gabe said, shoulders dropping with relief.

Sam walked into the back room, then right back out again without ever changing out the bread. "Here you go," he said, handing the bag to Gabe.

Gabe looked it over closely, sniffing and peering into the bag. "Thank you. This is much better."

"You're welcome," Sam said, trying to keep his smile from turning into a chuckle. "Have a nice day."

"I will now!" Gabe said, then headed for the front of the store.

Sam found Ash and told him that the problem customer preferred dealing with him, so not to even bother trying to please him. Ash hugged him.

*

"This bacon smells funny," Gabe said, waving the package of bacon in Sam's face. "Do you like bacon? I really like bacon, and it smells funny."

Sam nodded. "I do like it. Haven't had it in a while because I'm on a tight budget, but yeah, I like bacon."

"Well here," Gabe said, handing him the package. "Toss this in the employee bin and get me a new package. I don't want to eat it because it smells, but I'm sure a less discerning nose like yours wouldn't mind eating it."

Sam chuckled as he took the package. "I'll bring a new one out. Just gimme a minute."

This time Sam really did toss the bacon into the refrigerated bin. If his customer wanted him to eat bacon, he'd have bacon for a few mornings. He worked hard, so why not?

"Yes!" Gabe said, sniffing at the new package and closing his eyes in pleasure. "Much better. Thank you, Sam."

"You're welcome," Sam said, then waved as the man took his basket of food to the front of the store.

*

"Which one would you eat?" Gabe said.

Sam turned around, laughing when he saw Gabe standing there with a bag of M&Ms in one hand and a bag of gummy bears in the other. "Uhm, well, I prefer gummy bears."

"Me too," Gabe said. "But smell this! And try squishing them through the bag. They're all hard!" he said as he tossed the M&Ms onto the shelf nearest him and thrust the bag of gummy bears at Sam.

"Yeah, they do feel a little stiff," Sam said, smirking. "But I think maybe you should get them anyway."

Gabe frowned at him. "Why would I buy stale gummy bears?"

"Because I like them that way," Sam said, "and when you come to dinner at my place, you can bring them for dessert."

Gabe's eyes widened, then a smile broke out on his face. "Was I too obvious?"

"Not at first, no," Sam said. "But if I take home any more food that's perfectly fine other than the fact that my favorite customer refuses to eat it, I might get fired."

"Oh!" Gabe said, eyes widening. "I didn't mean to get you in trouble."

"You didn't," Sam said, shaking his head. "In fact everybody here is thrilled that I volunteer to take care of you every time you come in."

Gabe chuckled. "So when am I coming over to dinner?"

"I get off early tomorrow night, so how about then?" Sam asked.

Gabe nodded. "Sure. Are you on or off campus?"

"Just off," Sam said. "I'm a few blocks away in a shitty little apartment."

"Any roommates?" Gabe asked, mischief in his eyes.

Sam nodded. "One, but she won't mind taking off for the night if I tell her I have a guest."

"It's a date then," Gabe said, taking the gummy bears away from Sam. "I'll bring these."

"Okay, see you," Sam said, giving him a little wave.

"See ya," Gabe said.

*

Gabe turned out to be a really great guy, and Sam had a lot of fun with him. He got along well with Jess, even going so far as to buy her a beautiful necklace with a funny little design etched into the back of it. She loved it and wore it all the time, even when she was sleeping.

She was still wearing the necklace when Sam waved goodbye to her, taking off with his brother after packing up the car with all his stuff, Gabe in the back seat as they headed off for a road trip across the United States, just the three of them, ready to find Dad.


	10. Mommy

**Summary for the Chapter:**

> Anon Request: I'd love to read about pregnant!dean started leaking milk from his flat chest. Sam seeing that, totally got turned on and having sex. After giving birth, Sam watches dean breastfeeding their baby and then Sam gets emotionally overwhelmed by that (feeling how beautiful mother dean is) If you don't mind, I also love some domestic fluff about Dean being Mommy, like the baby starts calling Dean mommy?

**Notes for the Chapter:**

>  **Warning:** There is NO SEX INVOLVING THE CHILD. They’re careful of the baby being inside Dean while they have sex, but that’s as much involvement as the kid has. The other scenes after the baby is born are completely non-sexual and used for heavy doses of fluff. Also **Sam/Dean incest**.
> 
>  **Tags for This Chapter:** Sam/Dean, Wincest, mpreg, pregnant!Dean, top!Sam, bottom!Dean, lactation kink (including Sam drinking breast milk), hand job, fucking/anal sex, fluff and cuteness.

Dean grunted as he rolled out of bed, an urgent need to use the restroom, and stood up, his back a little sore. He was tired, had only been asleep for a little over two hours after a long day of work.

"Y'okay?" Sam asked from the bed, blinking up at Dean.

"Yeah," Dean said, rubbing his pregnant belly. He was almost seven months along, and already he was big enough that getting out of chairs and up off the bed was a bit of a struggle. "Gotta piss."

"'K," Sam said, rolling over.

Sam had worked even more hours than Dean, but he'd still made them both dinner and had rubbed Dean's feet before they both drifted off to sleep. Sam was very attentive and, had Dean been the type to ask for much of anything, Sam would've done anything for him.

Dean ran his fingers through his hair, scratching at his scalp as he walked back into the bedroom and lowered himself to the mattress. He'd just gotten comfortable when he felt a strange sensation.

"Aww, man," Dean whined, rubbing at his flat chest and finding dampness on his shirt. His pregnancy hadn't been easy, and he was uncomfortable a lot of the time, so to have a wet shirt when he was ready to just sleep was annoying and the last thing he wanted to deal with.

"What?!" Sam asked, bolting upright in bed and turning to Dean with wide eyes.

Of course it wasn't until then that Dean realized why his shirt was damp and he had the odd feeling in his nipples. "Oh!" Dean said, eyes about as wide as Sam's. "I... My milk just came in!"

Sam blinked at him for a moment, then smiled. "Yeah?" he said, then reached up and gently ran a finger around Dean's left nipple.

Dean hissed, back arching. When Sam pulled away, wounded expression on his face, Dean chuckled. "It's okay. They're just really sensitive. I felt that in my dick."

"Oh," Sam drawled, then grinned. "So if I were to play with them," he said as he barely touched the tip of Dean's nipple through the shirt, "then you'd be okay with that?"

Dean snorted. "Hell yeah! And dude, my milk came in. I can breastfeed the baby," he said, the expression on his face changing from turned on to sappy and near tears in less than a second.

Sam smiled. "I knew you'd be able to. I had no doubt about it."

"Yeah, well, some guys can't," Dean mumbled, trying to wipe the moisture from the corners of his eyes without making it obvious. He didn't like the mood swings, even though Sam said it was normal and not to worry about it.

"You're going to nurse our baby," Sam said, leaning down and placing a very gentle kiss on Dean's chest just below the nipple. "You're gonna be a mommy."

"Shut up," Dean grumbled. "I'm not a girl."

Sam kissed him again in apology. Dean had been grouchy about that fact from the moment he realized he was pregnant, but Sam could tell Dean was actually excited about it, he just didn't want to appear weak. That was okay. Sam would handle this however Dean wanted him to. Sam never thought women were weak anyway, and once the baby came, Dean would probably see how awesome it was that he was a mommy.

"I know," Sam said, then stuck his tongue out and slowly swiped over Dean's left nipple through the fabric of his shirt.

"Oh, fuck, Sammy," Dean groaned.

Sam's cock twitched, already hard just from seeing Dean leaking all over his shirt, from seeing Dean's reaction to being touched. "Feel good?"

"Yeah," Dean said, wrapping a hand around the back of Sam's head and pulling him closer. Sam covered the nipple with his mouth and started a very light suction. "Ah! Sam!"

Sam pulled back, smiling, because that was definitely pleasure, not pain. "Let's get this off," he said, grabbing the hem of Dean's shirt and pushing it up.

Dean sat up a little and let Sam pull the shirt over his head and toss it on the floor. Sam stretched out beside Dean and threw his right leg over Dean's, then rested his right hand on Dean's big belly, always careful about anything strenuous and wanting that reassurance that they weren't disturbing the baby. He put his mouth around Dean's nipple again and sucked, moaning when a little bit of milk came out.

"Ah, fuck, Sam," Dean moaned, back arching again as his right hand grabbed a chunk of Sam's hair and yanked.

Sam grinned at him. "Too much?" he asked.

"The vibration was a bit much," Dean said. "But I liked the rest of it."

"Okay," Sam said, nodding, Dean's hand still holding a chunk of his hair.

"Does it taste good?" Dean asked, wincing a little.

And right there is where anybody but Sam would've dropped the ball. Dean was insecure, worried he wouldn't be a good parent, wouldn't be able to give everything to their child that they could ever want or need, and to answer Dean honestly would've crushed him.

"It's perfect," Sam said even though it wasn't all that great. Sure, it was fucking hot as Hell, but the taste was a little too salty, a little too acidic. It wouldn't be by the time the baby was born, but this was Dean's first discharge, and Sam knew it was to be expected.

Dean smiled, relieved. "It feels good," he said.

"More?" Sam asked, smirking.

"Uh-huh," Dean said, nodding as he pulled Sam's head back down to his chest.

Sam used the flat of his tongue to swipe over the entire nipple, broad strokes that had Dean writhing. More of Dean's milk leaked out, and even though it wasn't the best taste in the world, Sam loved it. It was because of their baby growing inside Dean that the milk was coming in, and that was such a huge turn-on for Sam. This man who meant everything to him, who was carrying their child, suffering with morning sickness and cramps and an aching back and mood swings and cravings and sore feet and feelings of inadequacy -- he was doing it because it was all worth it, and Sam couldn't possibly love him more.

Sam's hand smoothed over Dean's belly and down under to Dean's cock, which was hard and leaking. Sam stroked him as he sucked on Dean's nipple, his own cock hard enough to hurt as Dean whined and spread his legs so Sam could have more access to his body.

"Sam," Dean gasped. "Sammy, please, I'm so fuckin' horny. Want you in me."

Sam was always hesitant to fuck Dean because of the pregnancy. He didn't want to hurt the baby even though he knew it was safe. But Dean had been amazingly horny throughout the entire pregnancy, so Sam had quickly learned how to make everybody happy.

"I've got you," Sam said, reaching under his pillow to grab the tube of lube he kept there at all times. "Turn onto your side a bit," he said, rolling Dean partially onto his left side before lifting Dean's right leg and draping it over his own.

Dean reached down to stroke his own cock while Sam opened the lube and coated his right index and middle fingers with it.

"Yeah," Dean encouraged as Sam pushed both fingers into Dean's ass, no need to stretch him much after all the sex they'd been having, the last time being just a few hours earlier. In fact, Dean was still a little wet. Sam worked in a third finger, then a fourth, but Dean was getting impatient. "C'mon! C'mon!"

Sam chuckled. "We'll get there," he said.

"Don't laugh at me," Dean grumbled as he elbowed Sam in the stomach.

Sam winced. "I'm not. It's fuckin' hot when you can't wait for me to slide inside you," he said as he pulled out his fingers and pushed his thumb in, rubbing hard on Dean's prostate.

"Sam!" Dean yelled, arching, his whole body going stiff.

"Easy, easy," Sam soothed as he kept rubbing.

"If you don't get your dick inside me within the next five seconds," Dean hissed through clenched teeth, "then you can forget about ever fucking me again."

Sam clamped his mouth shut so he wouldn't laugh. It was an empty threat, and it was really fucking adorable. "All right," he said, pulling his thumb out, then lining his cock up and pushing it inside Dean. He didn't fuck into him fast, but he didn't give Dean any time to adjust either. It wasn't much of a stretch, but Dean still hissed.

"Fuck, yeah," Dean said, finally smiling again. "Now fuck me!"

Sam grinned, glad that Dean was facing the wall and couldn't see it. He stroked Dean's cock a few times, the remaining lube on his fingers slicking up Dean's cock. But he still had to check, so he let go of Dean's cock long enough to lay a gentle hand on Dean's belly, making sure that the baby was quiet.

"The baby's fine," Dean said, and Sam could hear the smile.

Sam fucked in and out, pace slow and steady as he wrapped his hand around Dean's cock again and stroked. He decided to shut Dean up by craning his neck and sucking on Dean's nipple again.

"Sam!" Dean yelped.

Sure, it was an awkward position, and his neck was going to be sore later, but Dean was clenching around him, writhing and moaning. It was worth it.

"You gonna come already?" Sam teased. 

"Mmm-yeah," Dean said, already too turned on to care about the jab to his lack of stamina. "Faster. Move already! C'mon!"

Sam stroked him faster, but he didn't fuck him any faster. He was so turned on that the slow pace was going to get him off, and even if it didn't, it wasn't worth hurting his kid to get rough.

"The baby's fine," Dean repeated. "Fuck me!"

"I am," Sam said, then sucked on Dean's nipple again.

Dean put his hand over Sam's right forearm and dug his nails in. "Faster. Fuck me faster. I wanna come and I can't come like-oh!"

Sam smiled around Dean's nipple as Dean finally stopped demanding and started just making noises that turned Sam on even more. The faster pace he used to stroke Dean and the fact that he was tightening his fist around Dean's cock made all the difference.

"Sam!" Dean cried out, hips moving as he pushed back against Sam, then fucked forward into Sam's fist. "Gonna come. Gonna come. Mmm, Sammy, gonna come."

Sam stroked him even faster, sucked even harder on Dean's nipple, and kept the rhythm of his own hips the same as he had all along.

"Sam!" Dean nearly wailed as he came, clenching so hard around Sam's cock that Sam let out a hiss and came at almost the same time, hips never losing their rhythm and Dean's ass so tight around him it almost hurt.

"Better?" Sam asked, hips finally slowing and coming to a stop, his cock still inside Dean.

Dean didn't respond, so Sam gently pulled out and let Dean roll onto his back. Yeah, Dean was already sleeping. Sam chuckled, shaking his head. Dean had already been exhausted, so it was no surprise he'd fallen asleep after his orgasm.

Sam grabbed a rag from his nightstand and cleaned them both up, being careful not to wake Dean even though Dean slept like a log when he was pregnant. He dropped the dirty rag onto the floor, then flipped the blanket up over both of them and snuggled up against Dean's side, his hand on Dean's belly again.

*

Sam got home after a long day at work, tired and hungry, ready to settle down. He knew he'd need to change diapers and maybe give the baby a bath because Dean would be even more tired, having been taking care of the house and the baby all day, but that was okay. Sam didn't mind.

He walked into the house, closing the door behind himself very quietly so he didn't wake the baby if he was sleeping, then left his shoes at the door, padding to the baby's room.

Sam's breath caught in his chest. Sure, he'd seen Dean breastfeeding before, but it never failed to take his breath away. Dean was sitting in the rocking chair, eyes half closed, head resting against the back of the rocking chair as he rocked their son, who was suckling on Dean's right nipple.

Dean had used a pillow underneath the baby to get him elevated enough to nurse. Not having low-hanging breasts meant men had to improvise a bit. The baby was in a onsie, feet kicking as he hungrily ate his dinner, his tiny fist scratching at Dean's chest as he gazed up at Dean.

Sam's eyes burned and his throat felt tight as he watched Dean nursing their child. It was beautiful. Dean was beautiful. Sam had his family. He had everything he'd dreamed of having when he was a kid.

He turned and walked to the bedroom, stripping down to his boxers and taking a piss before he headed out to the kitchen to start dinner, wiping at the tears forming in the corners of his eyes.

*

"Muh, mmm-muh," the baby said.

Dean frowned at Sam. "What have you done!?" he said.

Sam held his arms out at his side, innocence written all over his face. Of course Dean knew Sam called him mommy and mama when he talked to the baby, but Dean needed to be the guy who grumbled about such things.

"Mah-m," the baby said.

"I"m gonna kill you," Dean hissed, then lifted the baby up, letting him practice standing on Dean's lap. He smiled at the baby. "What a big boy. Trying to talk. Can you say dada?"

"Muhm," the baby said, more of a humming sound than anything else.

Sam sat down next to Dean on the couch and smiled at his son. "Who's this?" he asked as he pointed at Dean. "Is this mama?"

"Sam," Dean hissed.

"M-maaa," the baby said, then looked at Dean's nose, poked at Dean's chin, and said very clearly, "mahma."

Sam cringed a bit, ready for an elbow to the stomach, but it didn't come. Instead Dean's breathing was a little ragged, and when he turned to look at him, there was a tear running down Dean's left cheek.

"That's right, little guy," Dean said, smiling. "I'm your mama."

Sam's smile was so big his cheeks were hurting.


	11. Us Against the World

**Summary for the Chapter:**

> Anon Request: I would really like Sam and Cas using Dean like a toy, for their own pleasure. DP, cockwarming, holding his ass open to be fucked, but lots of love and aftercare at the end!

**Notes for the Chapter:**

>  **Warning:** Nothing.
> 
>  **Tags for This Chapter:** Sam/Dean/Castiel, Wincestiel, switching (all of them top, all of them bottom), DP (two holes)/spitroasting, cockwarming, fucking/anal sex, blowjob, D/s, fluff, Dean being used as a living toy (fully consensual), actual toys including a ball gag and riding crop, very mild cock and ball torture (CBT), facefucking, gagging

Dean was kneeling on the floor in the middle of the motel room, hands clasped behind his back, naked with a ball gag in his mouth, drool running down his chin and dribbling onto his chest, cock standing at attention, legs spread, and eyes on the wall in front of him.

Sam was still in the shower, washing the grave dirt off, but Cas was teasing. Dean wanted to close his eyes, but that wasn't allowed. His cock was leaking, so hard it was red and sore, and if Castiel didn't stop soon, Dean was going to start whimpering and break position.

Cas had discovered sex toys. Well, okay, he was older than Dean wanted to think about, and Cas knew what sex toys were, but he'd recently discovered how much fun it was to use them. The riding crop tickling the underside of Dean's cock was Cas' new favorite toy.

Dean sucked in through his nose, flinching as the flat of the riding crop slapped his balls. He hadn't expected it, but it didn't really hurt much.

The thing is that Cas wasn't even looking at him. He was playing with Sam's laptop while sitting at the little table in the motel room, facing the same wall Dean was, and his left arm was on the arm rest of the chair, his wrist barely moving, like it was an unconscious thing to tease the shit out of Dean's cock and balls with the stupid fucking riding crop.

> _ice cubes moving over sam's skin, shivering, goosebumps, cas kissing and licking his way up sam's stomach until he sucks at the hallow of sam's throat, dean's fingers deep in cas' hole, making him squirm, cock leaking on the bed_

Dean held position, a drop of sweat running down the right side of his face. He almost sighed with relief when he heard the shower stop, and soon Sam was walking out of the bathroom, wiping himself down with a towel before tossing it in the corner and walking up to Dean.

Sam wrapped a big paw around his right biceps and pulled him up. Dean grunted as he got to his feet, his dick smacking into his stomach as he moved, turning him on more. He got to his knees on the bed when Sam directed him.

"Ass up, chest down, hands spreading yourself open," Sam said.

Dean's cock twitched as he got into position. Sam and Cas were only like this with him when it was play time, and Dean loved it. Being treated like an object, a toy, put into any position they wanted for whatever they wanted with very minimal verbal instructions let him forget who he was for a while, let him get lost in the arousal and obeying orders. A command he could follow immediately, knowing that he was doing exactly what Cas and Sam wanted was such a relief.

Sam climbed onto the bed behind him and pushed some cold lube into his asshole. Dean squeezed his eyes closed and was able to stay in position as Sam just fucked into him, bottoming out and groaning while Dean focused on opening up for him, keeping his ass cheeks spread, and staying right where Sam told him to be.

> _cas crying out as sam sucks him to yet another orgasm, his fourth one of the night while dean fucks sam from behind, and cas is still hard, still ready, still begging sam 'don't stop, just don't stop'_

Dean spread his legs a little more, shivering as Sam wrapped a hand around each of his flanks and started yanking him back with each thrust. Dean's cock was drooling on the bed and swinging forward and back with the force of Sam's movements.

Sam wasn't talking to Dean, wasn't giving him a reach-around, wasn't even touching him other than to push him this way and that so he could fuck him harder, and Dean loved it. He knew Cas would be watching, even if both of them claimed they were simply viewing him as a toy during play. He knew both Cas and Sam got off on it just as much as he did.

"Ah, fuck, yeah," Sam groaned as he pounded into Dean, coming deep inside him. He pulled out all the way, then got up off the bed to wipe himself down, leaving Dean on the bed, Sam's release running out of his hole and down his right inner thigh.

Dean stayed in position. He hadn't been told to move. The buckle behind his head was suddenly loosened and he let the ball fall out of his mouth, working his jaw and swallowing to get rid of the excess spit.

"My cock is cold," Cas said, as if he was mentioning some random fact he'd found on the Internet.

> _dean peppering sam's skin with kisses and soft touches as sam loses his virginity to cas, breath stuttering as he's overwhelmed by the presence of something older than the town they're staying in, something bigger than skyscrapers, something that's gently easing into sam, telling him how much he loves him, telling him to relax, that he'll take care of sam_

Dean crawled off the bed and sat on his heels between Cas' legs under the table. Cas didn't open his slacks, didn't even acknowledge that Dean was under there. Dean pulled Cas' cock out, smirking when he saw how hard he was. Cas _had_ been paying attention to Dean getting fucked.

Cas' cock was too erect to comfortably swallow and just sit there like that, so Dean took in what he could while still being able to breathe and just waited, warming Cas' cock for him. Cas didn't lose his erection at all, and Dean just concentrated on being good for Cas, forgetting about everything else.

Even though Cas was making noises every once in a while and tapping on the keys infrequently, Dean had no doubt Cas' mind was mostly on him.

"There's a hunt in Ohio that looks interesting," Cas said, voice a little strained.

Dean hummed around Cas' cock, giving himself a figurative pat on the back when Cas gasped and his cock twitched in Dean's mouth.

> _cas experiencing his first blowjob, hips thrusting forward, sam gagging on cas' cock, cas' eyes going wide, an apology on his lips that turns into a whimper as sam just starts sucking again and dean whispers dirty things in cas' ear, pinching his nipples from behind and riding the crease of cas' ass, cock hard and leaking on cas' back_

"What did you find?" Sam asked as he stood up from the bed and came up behind Cas.

"Huh?" Cas said.

Dean wished he could see the dazed expression on Cas' face.

"What's the hunt?" Sam asked.

"Bear atta-ah! Attack. Bear att-attacks," Cas stuttered.

Dean almost choked on Cas' cock as his hips jerked forward. Dean didn't care. It was a huge turn on to get that reaction out of Cas after adding some suction to the cock warming he was already engaged in.

"C'mon, Cas," Sam said, and Dean could hear the laughter in Sam's voice.

Dean frowned as Cas pulled out and stood up. Then Sam was yanking him up by the arm and bending him over the table.

> _sam realizing there are two people that make him complete in the middle of getting the best rimjob of his life from a being that he could only hope existed just a few long years ago, a being who is stealing his heart and soothing the pains from lovers who didn't care enough to die for him, dean more than just a little amused by the fact that sam forgets to keep fucking him when cas shoves his tongue into sam's hole_

"Which end do you want?" Sam asked as he picked up his laptop and set it on the chest of drawers.

"Oh," Cas said, almost a whisper.

Dean bit his lip as Cas pushed his cock in, sinking deep into Dean's ass. There was more than enough lube leftover from when Sam had fucked him, so Cas just started fucking, a slow drag in and out that Dean knew would drive him crazy.

"I get the other end," Sam said, lifting Dean's head with a hand under his chin and pushing his cock into Dean's mouth with the other hand. Dean readjusted himself a little, stretching out more so that he could angle his neck and take Sam's cock easily.

When Sam put a hand on the back of Dean's head, he knew it for the warning it was and took a breath in just before Sam pushed all the way in, Dean's nose pressed up against Sam's skin. Dean forced himself to stay still, to not freak out, fighting the urge to pull back.

"Don't you want to take off any of your clothes?" Sam asked Cas, chuckling.

"No," Cas said. "I like giving the toy rug burn."

Dean started to choke on Sam's cock, not so much because he needed air yet, but his throat just didn't want to cooperate anymore. Sam let him gag a few times, then pulled back. Dean gulped in air and coughed a couple times.

> _the look of surprise on cas' face when sam comes without ever touching his own cock, the only thing pushing him over the edge the fact that cas is touching him everywhere else -- sucking, licking, biting, pinching, rubbing, grinding, loving while dean sits on his heels, so close to sam that his knee is up against sam's right shoulder, not surprised in the least because dean always knew this could happen, that they could be like this, just the three of them_

"He's clenching around me," Cas hissed through his teeth.

Sam gave Dean's hair a tug, then started to push in again. Dean took a deep breath and let him in all the way. Cas' thrusts shoved Sam's cock further down his throat, his nose pressing harder against Sam's skin. Sam pulled out the first time Dean gagged, gave him another hair tug, then pushed right back in.

"C'mere," Sam said.

Dean didn't know what was happening until he heard Cas whimper, his thrusts stuttering to a stop as they squished him between their bodies, kissing above him. Dean loved listening to them kiss. Sam tended to be rough, use his teeth, and Cas would get overwhelmed in a good way, whimpering, gasping, making little noises almost as if he was in pain, but they were so fucking hot that Dean could listen to his brother and Cas kissing for hours.

Sam pulled back just as Dean started to gag. "Think you can come with me?" Sam asked.

Cas didn't respond, but Dean figured Cas was nodding, because soon both of them were fucking him, Cas' thrusts faster, more urgent than they were before, and Sam cradling both sides of his head as he fucked Dean's face.

Dean gagged and choked, but just kept breathing when he could, Sam timing his thrusts in such a way that Dean could keep up.

> _sam smirking, a dirty little smile directed across the room because he knows how much they're turning dean on, how it's driving dean crazy to kneel there quietly while cas rides sam's cock, his moans and whimpers filling the air, and dean can see it all, including the promise in sam's eyes that dean will be rewarded for being such a good boy_

"C'mon, Cas," Sam said, voice strained. "Wanna watch you come."

"Oh, Sam," Cas moaned, his fingers digging into Dean's hips as he fucked harder and harder.

The table groaned under the pressure of three men having their way with each other on top of it, but Dean didn't give a shit. He was focused, surrounded by the people who meant the most to him in the world, and at the end of it all, he knew he was going to be sated, happy, and conked out on the bed in a pile with those same two people.

"C'mere," Sam said, and Dean winced as again he was squished between them.

Cas let out a yelp, and then he was coming, crying out into Sam's mouth while Dean gagged on Sam's cock spilling down his throat. Dean knew Sam was pinching Cas' nipples. It was a sure-fire way to get him to come if he was right on the edge. He wished he could see it, but he was too busy trying to swallow and breathe.

Sam and Cas pulled out and instantly they had their hands on him, the entire mood of the room changing as they picked him up and carried him to the bed.

Dean was panting, trying to get his breathing back under control, but soon he was lying on the bed, Cas and Sam right there with him, Cas between his legs and Sam biting and nipping at his chest, his neck, his jawline, his earlobes, and any other spot he could get to that would get Dean going while Cas sucked his cock and shoved two fingers inside his messy hole, ruthlessly rubbing over his prostate until Dean came with a long, drawn out groan.

Sam and Cas flopped down onto the bed, Cas on Dean's left and Sam on his right, and they took their turns kissing him before kissing each other over him, Sam chuckling when Cas bit his lip hard enough to hurt.

Cas nuzzled at Dean's neck, then whispered into his ear. "Sleep."

Sam wiped a splotch of his come off Dean's cheek, then said, "We've got you. Go to sleep."

They each threw a leg and an arm over Dean and snuggled up, tracing patterns on his skin as their breathing evened out, all of them falling asleep soon after, sated and happy.

> _the realization that all of them fit together so well, that even though dean had been their first loves, sam and cas are in this for each other too, because as much as time and fate fights against it, this is it, them against the world, against the bad guys, and everything that has been meant to drive a wedge between them only makes their bond stronger_


	12. Lies and Break-Ins

**Summary for the Chapter:**

> **[majesticduxk](http://majesticduxk.tumblr.com/)'s (majestic_duck) Request:** ok, I have a prompt! if it so inspires you... something d/d with a punishment spanking, and Dean being the spankee. I prefer slash, but am happy for him to be paired with whomever, and you can take it where you want.

**Notes for the Chapter:**

>  **Warnings:** None.
> 
>  **Tags for This Chapter:** Sam/Dean/Castiel, Wincestiel, no sex, domestic discipline/discipline spanking, swearing. It’s not excessive discipline and it’s done with love. This can be read as gen!fic, but I know duck likes Wincestiel :)

"Rest assured he'll be getting a spanking when we get home, ma'am," Castiel said to the woman, who was soaked in pickle juice.

She blinked at Cas while Dean's eyes widened and his jaw dropped. The woman was in her late seventies, and she'd lived in a time when that sort of thing wasn't so shocking, so she recovered much faster than Dean did.

"See to it that he does," the woman said, pushing her wet hair back and wiping at her face. "I don't know what he was thinking, but if I ever see his face again, I'm calling the police!"

"He's very sorry," Sam said, putting a hand on Dean's neck and squeezing just enough that Dean got the message.

"I'm very sorry, ma'am," Dean said, ducking his head. The blush was genuine.

"Of all the bullshit I've heard over the years," the woman said, shaking her head as she eyed Dean, "a satanic ritual room in my basement because I'm supposedly a demon or a witch is new to me."

"I'm really sorry," Dean said.

"It never occurred to you," the woman said, getting a little closer to Dean, scowling at him, "that perhaps all of my 'suspicious purchases' were because I was canning the fruit and vegetables from my garden?"

"No, ma'am," Dean said, sheepish look on his face.

"And you didn't even bother to pay attention to the fact that all my windows and doors are salted and the basement is full of protective sigils carved into the baseboards and door casings," she huffed, then turned and walked back into her house, slamming the door.

Dean cringed. "Shit."

"Yeah," Sam said, crossing his arms over his chest, "you _didn't_ know she was a retired hunter."

"Which means you didn't bother to do any research on her past," Cas said.

"Oh, c'mon," Dean said, frowning at the both of them. "You've gotta admit the basement was really fuckin' suspicious."

"Dude, she's got her own website," Sam said. "She runs a blog on hunting. You're lucky all she did was lock you in the basement until we talked her down."

"Oh," Dean said, shoulders dropping. He turned to Cas. "So it was an honest mistake. I didn't know."

Cas turned and headed for the car, Sam letting out a huff and following just moments after.

Dean stood there, unable to move until Cas turned to glare at him. "Coming. I'm coming."

The car ride back to the motel was quiet and tense.

*

Dean sauntered into the motel room, and even though it appeared he was fine, he was freaking the fuck out. He hated disappointing people, especially people he loved.

Cas took his coat off and draped it over the luggage rack, kicking his shoes off before he loosened his tie, tossing it over the coat. Dean started to squirm in the middle of the room when Cas unbuttoned his cuffs and rolled up his sleeves. But then Cas reached into Sam's duffel.

"Look, I know I fucked up," Dean said, holding his hands up, "but let's just talk about this."

Cas pulled the hairbrush out of Sam's duffel and turned to Dean, patient yet firm. "Okay."

Dean winced. Cas had never just gone after him for no reason, and really he should've expected that Cas would be open to discussion, as usual, but he had nothing. No excuses for what he did, and no way of talking himself out of what was coming.

Sam hung the 'do not disturb' sign on the door handle, then closed and locked the door. "You lied. Multiple times to both of us."

Dean looked down at the floor, cheeks heating up, because yes, he had lied. To both of them. Multiple times. "I've been a hunter longer than the both of you," he said, "and I really thought I had it. The neighbors were suspicious, she had some herbs growing in the garden that most people have never even heard of, and she works on her canning at night in the basement. What was I supposed to think?"

"You were supposed to do research," Cas said.

"Like you said you did," Sam said.

"I did," Dean lied, shrugging. Hunter's intuition had been his research, as well as talking to the neighbors. "I just didn't find anything that led me to believe she was a hunter."

"Research doesn't mean stalking her," Sam said.

"Okay, then where did you find the information about her being a hunter?" Dean asked, ready to give Sam an 'I told you so.'

"I Googled her name," Sam said. "She's open about it. She even has a Q&A section for other hunters."

"Oh," Dean said, then sighed. "Well, I'm not as good at finding that stuff as you are."

"Which I would've done had I known you were lying when you said you'd done the research," Sam said.

"We don't lie to each other," Cas said, voice low.

Dean felt the words in his chest, like someone had punched him. "I'm sorry," he said, the wind knocked out of his sails.

"Take your jacket off," Cas said, then gestured to the chair set by the small table. "Jeans and underwear down, then bend over the chair."

Dean felt like shit, but it was hard to just present himself for discipline. It hurt, and his pride always took a hit when Cas brought him to tears while Sam stayed close by. Dean flinched as Sam came up behind him and started pulling his jacket off.

"Dude," Dean complained, moving forward, but still letting Sam take the jacket off and toss it on the bed.

Sam knew Dean would freeze, that sometimes he needed a little incentive to get moving, and Sam hated when Dean got in more trouble because he didn't follow orders.

"C'mon," Sam said, reaching around him and undoing his belt.

Dean leaned back, drinking in the warmth from his brother. He felt jittery and his ass cheeks were clenching as he looked at the hairbrush in Cas' hand. It was oval, bristles having never touched hair, because Cas had gotten it just for using on Dean. The wood had a shiny coating, some kind of sealant that allowed Cas to keep it clean and helped make it stronger.

His knees felt weak as Sam unbuttoned the jeans, lowered the zipper, and began pushing the jeans and underwear down Dean's legs. Dean pushed back into Sam as Cas took a step toward them, but before he could get himself in more trouble, Sam was pushing him down, his hands on Dean's back and arm, positioning him bent over the chair. Dean put his hands flat on the seat, the scratchy, faded material nothing interesting, nothing he could really focus on to get his mind off what would be happening.

"Why are you getting a spanking?" Cas asked, putting his left hand on Dean's lower back and rubbing the flat of the hairbrush over Dean's left ass cheek.

Dean's junk was squished against the back of the chair, so he squirmed a little until it wasn't digging into the edge, spreading his legs some. His knuckles turned white as he got a good grip on the cushion.

"I lied," Dean said.

The next second he was going up on his toes because Cas was hitting him hard and fast. Yeah, Cas was not happy about the lying. He didn't start with a warm up hand spanking, but went directly to using the hairbrush. Dean tried to settle, knowing that he'd brought it on himself by betraying the trust Cas and Sam had in him.

"Sorry," Dean said, shifting from foot to foot, hoping to alleviate the sting building up in his ass.

Cas was methodical, his strikes evenly spaced and in a rhythm that was harder to take than random hits. Dean knew exactly when each one would come, where it would come, and it made him focus, made him anticipate, which made it even worse.

"Did I not get through to you last time?" Cas asked.

They didn't throw things in each other's faces. Bringing up the past over and over again wasn't their thing, but problem areas had to be mentioned, and lying was something that could tear them apart.

"You did," Dean said through clenched teeth, twisting a bit so that his ass moved away from Cas, but he didn't really get anywhere because Cas wrapped his left hand around Dean's right side, keeping him in place.

"I must not have," Cas said as he started in on the undercurve of Dean's ass cheeks.

"No! You did! Really!" Dean said, going up on his toes again.

"But you did it again," Cas said.

"I know," Dean said, ducking his head and squeezing his eyes shut against the burn. "I'm sorry."

"We're a unit," Sam said, and Dean sucked in a gasp, because he was fucking close.

Dean opened his eyes and lifted his head, looking directly into his brother's eyes, who was kneeling in front of him. Dean opened his mouth, ready to tell Sam to get the fuck away, that this already fucking sucked, and that Sam wasn't helping, but he realized that was the point.

"Secrets and lies hurt us," Sam said.

Dean let out a whimper as Cas started on his upper thighs. "Fuck, Cas, c'mon."

He bent his knees, pulling down some, his ass lowering. It didn't stop Cas' assault on his ass, but Dean couldn't keep still anymore.

"I'm sorry!" Dean said, and winced at the emotion in his voice, the tears welling up in his eyes frustrating him.

Cas started up at the top again, that maddening rhythm almost unbearable as the pain built up. Dean's bottom lip wobbled and he bit it, trying to stay in control. He hated losing that control, hated blubbering in front of Sam and Cas, and if he could just take his punishment, then he could apologize and climb into bed.

The rhythm was a torture in and of itself, and it only added to the pain. Sam was kneeling in front of him, concerned expression on his face, that look he always got when Dean was getting his ass beat for something, like Sam really didn't want it to happen but knew it was necessary, and Cas behind him, hurting Dean when he really hated it, hated making Dean cry, hated leaving Dean's ass red, but all three of them having agreed to this, seeing how well it's worked.

Dean felt a few tears run down his nose and drip onto the cushion below him as Cas started on the undercurve of his ass again.

"If you didn't want to do it, I'd've done the research," Sam said.

Dean went up on his toes again, trying to get away from the burn that he could feel all the way into his throat. "It's not the-ow! It's not... fuck. Ow. Fuck, Cas. Ow. I just... I thought I fuckin' knew," he blurted.

"Oh, you didn't think you _needed_ to do research," Sam said, one eyebrow twitching up.

"Ow!" Dean bellowed as Cas started hitting harder. "Oh, fuck," he groaned, lifting his right foot up. He didn't know what it would do, but it hurt way too much to stay still. He twisted, squirmed, arched his back, squeezed the cushion even harder.

Cas held on, kept spanking. "We've talked about this before."

"I know!" Dean nearly growled. "I'm sorry. I j-oh, fuck, ow! I'm really fu-ow! I'm so fuckin' sorry! Jesus, Cas, I'm s-ow! I'm sorry!"

"Research is necessary," Cas said, starting over at the top of Dean's ass.

"No," Dean whined, not really denying the research so much as he was objecting to beginning at the top of his ass again. "Please, Cas."

His ass had to be bleeding. He just knew it. It was on fire. His skin had to be falling off. It never had before when Cas spanked him, but it fucking hurt.

"We've gotta be able to trust you," Sam said.

The words really didn't make him start crying. No, really. Okay, so maybe it hurt inside his chest, an ache that took his breath away, and then he was crying, sobbing, his face a mess of tears as he tried to remember how to breathe, his body shivering, legs shaking from the pain, throat and eyes burning because of the realization he was hurting the two people he loved most and who were always there for him.

Cas was rubbing his back, Sam was cupping his face, holding him up, then Cas was pulling his shoes, socks, jeans, and underwear off his feet, then Sam was helping him stand up straight, taking his shirts off, and Cas was wiping his face with a cool, damp washcloth as both Cas and Sam led him to the bed, lowering him down as they climbed on too. Cas spread out on his back, arms open and welcoming as Dean dropped down on his right side, using his arm and upper chest as a pillow, tossing his right leg over Cas' as Sam settled down behind him and stroked his back with gentle touches, placing a few soft kisses on his back while Cas stroked Dean's face with the fingers of his left hand.

"I'm sorry," Dean said.

"You're forgiven," one of them said. He didn't even know who it was, didn't care, because they both meant it, and he was crying again, closing his eyes as they just continued stroking him, loving him, and that was all Dean needed.


	13. More

**Summary for the Chapter:**

> **[Anon Request](http://mayalaen.tumblr.com/post/128004500299/i-was-just-on-archive-of-our-own-and-i-wanted-to):** I was just on archive of our own and I wanted to request something. Can you make cas have a gaping ass hole that never closes and that needs to be filled up with a butt plug all the time and when dean has sex with him he has to have something else.

**Notes for the Chapter:**

>  **Warnings:** None.
> 
>  **Tags for This Chapter:** Dean/Castiel, anal gaping, stretching, sloppy hole, toys, object insertion, fucking/anal sex (kind of), handjobs, porn watching, butt plugs

It all started with porn. As most things do between Dean and Cas. Dean's watching it, Cas is interested because anything involving Dean and sex is something Cas finds really fun, so he's leaning over Dean's shoulder before Dean even realizes he's there.

"He'll never regain full muscle tone," Cas comments.

Dean jumps so badly he bites his own lip. "Jesus, Cas. Warn a guy!" he says, hand over his heart as he tries to calm himself down.

"Do you find this sexy?" Cas asks.

Dean smirks, because yeah, Cas has started using words like sexy and fuck and cock and it's so fucking hot coming from the mouth of an angel, a dirty kind of thing that gets Dean going in record time.

"Yeah, I've got a bunch of bookmarks for gaping," Dean says, opening the folder with nearly thirty bookmarks in it.

Cas peers at each bookmark as if he's watching each video as he reviews the list. And for all Dean knows he is. "Would you like to do this to me?"

Dean chokes. "Really?" he asks, not quite sure if Cas has been around him long enough to tease him like this or not.

Cas turns to him. "I have complete control over this vessel. I can make it do anything."

Dean's cock is getting harder. "Uhm, well, okay," he said, nodding and already imagining all the fun he's going to have.

"Do we need those toys?" Cas asks, pointing at the screen where a man is lowering himself onto a traffic cone.

"No," Dean says, shaking his head. "I mean we _do_ need toys, but I don't really find a bright orange cone all that hot."

"Which ones do you find hot?" Cas asks.

Dean grins. "Those and that and that one," he says, pointing to a few different items on the wall of the playroom on the screen.

The next second Cas is gone, and Dean stands up to strip, because Cas won't be gone long. Sure enough, Dean's yanking off his socks when Cas comes back with a large black shopping bag.

"The cashier was very helpful when I read his mind," Cas says, dumping everything out onto the bed.

Dean's jaw drops. "You paid for this, right?"

Cas rolls his eyes. Another thing he's picked up from Dean. "Yes," he says as if Dean's being particularly stupid.

"You're fast," Dean says.

Cas shrugs. "It seemed like a half hour to the cashier. He noticed nothing out of the ordinary."

"Cool," Dean says, then picks up a long string of anal beads, conveniently in graduating sizes.

"That would be the toy the cashier suggested when I told him I wanted to gape, but had never done so before," Cas says, handing the string to Dean.

"Did you get any lube?" Dean asks, already playing with the beads, feeling their sizes and enjoying the smoothness of the surface.

"I'm going to be manipulating this vessel," Cas says. "I won't need lube."

"Ah, Cas, you kinda need lube," Dean says.

Cas gives him a look that says he really wants to roll his eyes, and Dean flinches when suddenly the beads in his hands are slippery with some kind of jelly-like substance.

"Oh," Dean says, eyeing the beads.

Cas mojos his clothes away and climbs onto the bed, spreading his legs and looking at Dean over his shoulder. "I'm ready."

Cas doesn't tease him when Dean comes in his pants after only the fourth bead slips into Cas' hole.

*

Dean reaches forward and smacks Cas' ass as they're walking up to the house of a woman who reported a monster outside her bedroom window. He grins when he can feel the base of the thick butt plug stuck up inside Cas.

Cas acts as if nothing happened and reads the mind of the woman before she even has a chance to ask them inside. Cas tells her she needs to check on the baby, so she says goodbye and closes the door.

Dean chuckles. "You take the fun out of interviewing people."

"I would've let you interview her if she hadn't been exposed to an eventually lethal dose of the drugs that were previously manufactured in her home," Cas says.

"Whoa, wait," Dean says, grabbing Cas' arm and turning him around.

"I cleaned the house and cured her as well as the baby," Cas says. "She was hallucinating. There was never a monster outside her bedroom window."

"You're awesome," Dean says, grinning.

"I'm also horny," Cas says.

Dean snorts. "What a coincidence. So am I." The next second they're standing in the motel room they'd been staying in. "My car," Dean says, not really upset, just reminding Cas.

"We'll get it later," Cas says. "I have something for you."

"Yeah?" Dean says, unbuttoning Cas' shirt. After a couple of arguments, which Dean won, Cas no longer mojos his clothes away. Dean likes unwrapping the package.

"It's on the table," Cas says.

Dean pushes the shirt and coat off Cas' shoulders, letting them fall to the floor. When he turns to see what Cas got for him, he frowns.

"I've got you," Dean says, holding his arms out at his sides. "I don't need a fleshlight. That's part of being in a relationship."

"You were having trouble getting enough friction to come because you've opened me up so much," Cas says as he walks to the table and picks up the fleshlight. "This solves that problem."

"Cas, it's okay," Dean says, shaking his head. "It takes me longer to come, but I love seeing you all wide and open for me. I don't wanna sit all by myself and fuck a tunnel."

Cas pushes the fleshlight into Dean's hands and smirks before breaking the rules and making the rest of their clothes disappear. He climbs onto the bed, already pushing the large plug out of his ass. It drops to the bed, leaving behind a gaping hole, dripping with lube and the last of Dean's early morning release.

"Put it in me," Cas says.

Dean frowns, then looks down at the fleshlight. "Oh, fuck," he breathes as he finally gets what Cas is saying. "Uhm, wow, okay. Yeah. Yeah," he says as he walks up to the bed.

Cas' hole is red and wet and so big that Dean can fit his fist and forearm in there without any stretching. Fucking Cas has still be fun, but as exciting as it is having him like this, Cas is right about the lack of friction.

Dean lines the fleshlight up with Cas' huge hole and pushes it in, the whole thing sliding in so easily it was like Cas was made for it. It should be ridiculous, it should make him laugh, but it doesn't. Dean wants him, wants to fuck Cas like this, and knowing that he'll be able to feel the tightness while still being inside Cas makes his cock twitch.

Cas is already hard and leaking. He can force his vessel to respond like that, but Cas says he's usually turned on enough by Dean that he doesn't have to force it. Dean climbs onto the bed behind Cas and pushes his fingers into the hole of the fleshlight, grinning when he finds it already lubed. The end sticking out of Cas is pink and looks like an asshole, but no way in Hell anyone would mistake it for Cas' asshole, especially not when Cas' hole is stretched around the toy.

Dean pushes his cock in, groaning when the thing is tight enough to require some effort getting in.

"Fuck me," Cas says.

Dean hisses as he starts moving, his thumbs on the edges of the fleshlight to keep it in place as he fucks it. Cas reaches down to jack his own cock, but Dean doesn't think that's very fair, so he wraps his left arm around Cas and pulls him up so they're both on their knees.

In this position, he's able to fuck Cas while playing with Cas' left nipple and stroking his cock. Cas pushes back as Dean fucks him harder, wrapping his hands around Dean's head and pulling him down to kiss him the best he can in the position. It's awkward, but neither of them minds it. Not when Dean is slamming into him, the toy making a loud squelching noise as it's pulled partially out of Cas' wet, loose hole, then back in over and over again.

"Feels too good," Dean says. "I'm gonna come."

"Please," Cas gasps, "come inside me."

Dean knows he's fucking a fleshlight, but for some reason it's even hotter that Cas is using it as an extension of himself, like the toy is now yet another part of Cas Dean has all to himself.

"Fuck, Cas," Dean nearly growls, fucking up into Cas hard enough that he's punching the breath out of Cas, the squelching so loud it's bordering on ridiculous, and Dean loves it all, fucking Cas as he come inside the fleshlight.

Cas whimpers as he comes, and even though Dean misses the fact that he can't feel Cas' asshole fluttering around him, the way Cas is practically writhing against him makes up for it.

Dean clings to Cas as he pants, catching his breath with his forehead on Cas' shoulder. But Cas is still moving, and Dean pulls back, frowning at him.

"Please," Cas says.

Dean huffs out a laugh. "You empty? Need a plug in that sloppy hole?"

"Yes," Cas says, and there's desperation in his voice, like he's scared of being empty.

Dean knows it's an act for him, but that makes it even better. Cas does this all for him, and Dean still can't wrap his head around it even after all this time. Dean yanks the fleshlight out of Cas while pushing Cas forward. Cas catches himself, spreading his legs and with his palms flat on the bed, ready for Dean.

"So beautiful," Dean says, because when he's just gotten laid and Cas is so fucking beautiful like this, Dean lets his walls down, and Cas never calls him on it, and instead smiles, an adorable little smirk that says Cas really likes being called beautiful.

Dean pushes their largest butt plug into Cas' hole, the black end of the plug the only thing visible as Cas wiggles his hips.

"Good?" Dean asks, caressing Cas' ass and thighs.

"Yes, Dean," Cas says.

"C'mere," Dean says as he flops down on the bed.

Cas snuggles up, already comfortable being the little spoon, and the two stay like that for a while until Dean falls asleep.

**Notes for the Chapter:**

> **A/N:** I have A LOT of kinks, but gaping isn't one of them. It doesn't squick me, it just doesn't do anything for me. I hope I did this one justice :)


	14. Doc

**Summary for the Chapter:**

> **[HollyBlue2's Request](http://archiveofourown.org/comments/33697956):** Maybe some doctor!top!cas  & bottom!dean with restraints, sounding, latex gloves and some good ole dirty talking? For a scene, maybe they've got a basement kitted out with some medfet supplies?

**Notes for the Chapter:**

>  **Warnings:** This is completely consensual, but Dean is scared of doctors, and when he freaks a little, he uses his “slow down” safeword/gesture.
> 
>  **Tags for This Chapter:** Dean/Castiel, AU, medical play/kink, roleplay (kinda), anal speculum, stirrups, restraints/bondage, sounding, handjobs, sounding.

Dean's shivering, a little nervous, but still excited if the full erection tight against his stomach is anything to go by. He's beautiful, my Dean. His eyes follow me as I walk around the examination table in our basement. He's strapped down tightly because Dean's actually terrified of doctors. Ironic that he fell in love with me.

"Are you cold, Dean?" I ask, pulling my white ear-loop mask down under my chin. I'm in blue scrubs, which adds to the mood of our game.

Dean shakes his head, indicating that no, he's not cold. He'd speak, but I've fitted him with a ring gag. It keeps his mouth open and vulnerable. I like using it because then I can hear every gasp, every moan, every whimper, every squeak with nothing getting in the way.

"What's wrong, then, sweetheart?" I ask as I pull a white latex glove onto my left hand, letting it snap and enjoying the way Dean flinches with the sharp sound.

"Asshole," Dean says, and it's only because I've known him so long that I can tell what the noises coming out of his throat mean.

"What was that?" I ask, teasing as I pull the other glove on.

Dean lets out a huff that's as close to laughing as he can get right now. He really is scared. He trusts me, but all the exposure he had to doctors at such a young age when his appendix burst inside him affected the way he views anyone in the medical field. He loves me, knows I love him, and that's the only reason he willingly gets onto my table, the only reason he agreed to turning our basement into a medical facility like this in the first place.

"Ass. Hole," Dean says. Okay, that time someone other than me might have been able to tell what he was saying.

"Name calling is very uncalled-for," I say as I reach for a speculum.

Dean's eyes widen. He really shouldn't have been surprised. His legs are strapped into stirrups, which should've clued him in, but as I've mentioned before, Dean is scared, and he's not thinking clearly.

"Cas," Dean says, but really it just sounds like ass.

"I need to make sure you're all right after I fucked you this morning," I say.

I know I didn't hurt him this morning, but it distracts him some, and it also reminds him of a time when he was getting off harder than he had in a long time. We take turns with our fantasies, and this morning was Dean's time.

"You remember that?" I ask.

Dean nods, a grunt coming from his throat that may have been yes, but also could've been just a pleasured noise as he thinks about fucking my face, the way I've trained myself to allow for rough treatment without my gag reflex kicking in.

"It's my turn," I say, a quick reminder that this is a mutually beneficial situation and nothing to be terrified of.

Dean nods again, understanding why I said it.

"Good boy," I say as I walk to the end of the table, between Dean's spread legs. Dean's asshole is clenching, anticipating the speculum.

I run my index finger over his hole, smiling when he flinches, pulling away, a gasp from him letting me know that he's a little too nervous. That's easily remedied. I lean down and suck his now half-hard cock into my mouth and give him some stimulation. He lets out a groan, his body relaxing again. I play with his balls, rolling them in my right hand.

As soon as Dean starts to squirm, I let his cock fall from my mouth and stand up straight again. His eyes are a little glazed, his cock hard again. I pull a tube of lube out of my pocket and hold up the speculum, squirting some of the lube onto the end. Dean's watching, his fingers tapping on the examination table in a nervous gesture.

"I'm going to examine your asshole now, Dean," I say, my cock hardening as Dean tenses, holding his breath. "Just relax."

Dean tenses more, so I just place the speculum against his hole, not pushing in just yet, and instead I run the tips of my fingers over his cock and balls, my right hand still holding the speculum against his hole.

"Relax, sweetheart," I say, then slowly push the speculum inside.

"Ah! Ah! Ah!" Dean yells, shaking his head back and forth, and I instantly freeze. It's not red, only yellow, and calling a yellow safeword doesn't require using my quick release features on my equipment.

"Dean, look at me," I say when I notice his eyes are squeezed shut. When I have his attention, I smile at him. "It's okay if you're scared. You're doing so well. You're so beautiful laid out on my table like this."

Dean closes his eyes again, but this time his body relaxes some, his breathing still a little rough.

"Look at me," I say, and when he does, I rest my free hand on his tummy. "If you want to stop we will."

Dean sighs, then shakes his head. "Sorry," he says.

"Nothing to be sorry for," I say, patient and calm because Dean needs it. "You can use your safewords any time you need to."

Dean nods, body relaxing even more. "Okay," he says.

"It's not going to hurt," I say. "I'm very good at my job."

Dean lets out another huff of laughter, and he'd be smiling if the ring gag wasn't stretching his lips so much.

"Relax," I say, then gently push again.

Dean gasps, but doesn't tense, and soon the speculum is all the way in. I start to open it, and Dean whimpers. I watch him carefully to make sure it's not a distressed whimper, but he's not tensing, he's not shaking his head, and his cock is still mostly hard.

"It's in and open all the way," I say, because Dean likes to know what's happening at all times, likes the dialog. He gets nervous when it's too quiet. "You're such a good boy for me."

Dean's body relaxes more, his cock twitching with the praise. My Dean loves to be praised, but it's only during play time that he'll allow it, only then will he squirm and lower his eyelids just a bit, basking in the compliments.

My next tool is sealed in an autoclave pouch, cleaned and sterilized for use. I open it, ripping the package and squeezing some lube onto it. Dean's shivering again, but it's not the first time he's experienced sounding. He loves it, and the shivering is excited anticipation instead of fear.

I hold his cock up with my left hand, then wave the sound over his cock, letting him get a good view of it before I squeeze the tip of his cock, spreading his hole. I let the end of the sound tease the rim of his slit, smiling when Dean's cock twitches. I push the sound into him, just a little bit, then let gravity work for me as Dean moans, the sound easily falling in, stopping at the flared end.

I only need one hand to hold his cock now that the sound is in, so I reach down with my right hand and insert my middle finger inside the hole created by the speculum, pushing down. Dean's reaction is nothing short of adorable, because one moment he's calming down and the next he's lifting his ass off the table as much as it'll go and letting out a pleasured moan.

"Feels good," I say instead of ask, because it's obvious he likes it.

It's a strange sensation. I know because I've had this done to me, and the first time is always the most exciting because after you've had it done once, you know to expect that strange sensation, the feeling of your body moving from the inside, that sensation of fullness and emptiness at one and the same time.

I lean down, wishing I could see Dean's face when I blow into the speculum, Dean's body tensing as he lets out another moan, his thighs shaking. I turn and kiss his left thigh, smiling against his skin when he starts whimpering. By the time I straighten again, his eyes are squeezed shut and he's nearly panting.

His cock is still in my left hand, and when I start stroking him, he lets out another long moan. The sound in his cock shifts, and Dean gasps, his ass coming up off the table again, but then he lets out a shocked yelp as I start tapping on the speculum with my right index finger.

I know this sensation too. The vibrations inside his asshole and body are going straight to his prostate, not as strong a sensation as rubbing directly over it, but rhythmically tapping like this can be almost too much after any length of time.

"After you come, I'm going to fill your hole with my own release," I say, and I know it's a brand new idea to Dean because he lets out a whimper, his cock twitching in my hand. He'd never thought of me jerking off into his hole while the speculum holds him open, and he loves it.

Dean cries out, the stirrups clunking as he writhes about, knocking them back and forth, his chest heaving as he pants.

"I don't even need to be inside you," I say, stroking him faster, "and yet I can still come inside your hole."

Dean tries to fuck up into my hand, but he's strapped down, so he's not really moving all that much, but he's close to coming, and so I start tapping even harder inside him. I pull the sound out of his cock and drop it on the table.

"Ah!" Dean nearly wails as he comes, his whole body tensing as he paints his stomach with his own come.

"Such a good boy," I say as I give his cock a few more tight pulls before I let go of it and quickly get my own cock out of my scrub pants. There's still lube on my right hand, and after watching Dean, it won't take me long anyway.

It only takes a few strokes and I'm coming, holding my cock to Dean's hole and grunting as my release goes inside Dean, just like I'd promised him. Dean's still panting, but he's watching, eyes on my face.

When I finally settle down I close the speculum and gently take it out of Dean. He gasps, then squirms at the empty feeling left behind. I pull off my gloves and drop the speculum and gloves onto the counter top to my left. Next I walk to the head of the table and unbuckle the gag, carefully taking it off Dean.

He works his jaw a bit, licks his lips, then smiles at me. "That was awesome," he says, slurring a little.

I let out a chuckle. "So this means you'll agree to a repeat performance?"

"Definitely," Dean says, nodding. 

"I thought you were scared of doctors," I say as I start to unbuckle the straps holding him down.

"Yeah, well, I think you're ruining that for me," Dean says, sitting up and stretching. "Maybe next we can work on my fear of rats."

I stop unbuckling his left leg from the stirrups, smirking at him. "And how would you like me to do that?"

Dean winces. "Can we just forget I said something so stupid?"

"Post-orgasm brain cloud?" I ask.

Dean nods. "Yeah. No rodents in our sex life, please," he says, letting out a huff of laughter.

"I wasn't planning on it," I say.

"Good," Dean says. "And you just remember that."

I help him turn so his legs are dangling over the edge of the table, then I wrap my arms around his neck and kiss him, the ear-loop mask a mild annoyance as his fingers get caught in the straps when he tries to pull me closer to him.

"So what are the results of my examination, doctor?" Dean asks when I pull away from the kiss.

"I think you'll live," I say, smiling.


	15. Daddy's Good Boy

**Summary for the Chapter:**

> **[IShipItAllAndThenSome](https://archiveofourown.org/works/4244124/comments/35014910)'s Request:** I kind of wanted to prompt something along these lines, but then I wanted to do it myself, but I still want to read your take on it, so here goes. Can I have Dom!Cas/sub!Dean with daddy kink (Daddy!Cas), praise kink, spanking, maybe a little exhibitionism (fucking by an open window or in an office - maybe Dean Smith verse with Cas as his superior? - or at a BDSM dungeon), and Dean being shy about his panties because he's never told Cas about them before? Sorry for the babble.

**Notes for the Chapter:**

>  **Warnings:** None.
> 
>  **Tags for This Chapter:** Dean/Castiel, It’s a Terrible Life AU/Dean Smith, daddy kink, boss/employee relationship, mild D/s, panties, dirty talk, handjob, erotic spanking, begging, fucking/anal sex, voyeurism, exhibitionism, praise kink, prostate massage/fingering

"Dean."

Dean flinched, then nearly fell on his face as he stood up. "Yes, sir?"

Mr. Novak closed the door to Dean's office, then walked up to the desk. "Did you finish that report?"

Dean couldn't remember what the fuck the man was talking about, and then he realized. His face felt hot, and his neck was a little itchy. Now? Of all the times Mr. Novak could've chosen, he'd picked today?

"Uhm, no, Daddy," Dean said, looking down at the floor as if he was ashamed. He wasn't really. He hadn't done anything wrong, and in fact he was about to get laid. His cock was already getting hard. But Cas didn't realize what was under the slacks.

Cas sighed. "Yes, you did, sweetheart," he said, walking around the desk and putting a hand on each of Dean's shoulders. "And you did a very good job."

Dean shifted from foot to foot. Yes, he had turned in a report the day before. And he'd been very thorough, but that didn't mean Dean wanted to hear all about how awesome it was.

"You did such a good job that I've come to give you a reward," Cas said.

Dean grinned as he looked up. "A sexy reward?"

Cas chuckled. "Yes."

Okay, so maybe Dean really, really liked getting praised. But nobody else needed to know that. And if Dean could spin it as a sexy-times thing, then it was all good.

"But you're wearing way too many clothes to get your reward," Cas said, frowning as he gestured toward Dean's slacks.

Dean felt his face heat up even more, his ears tingling. He opened his mouth, but nothing came out.

"Something wrong?" Cas asked.

"N-no, Daddy," Dean said.

"You don't have to be shy around Daddy," Cas said, smiling.

Dean's cock twitched. He couldn't help it. Cas did things to him that no one else had ever done. And Dean loved it.

"If I have to take your slacks off for you," Cas said, taking another step closer, "then I'm going to have to spank you."

Dean squeaked. He fucking squeaked as his cock started to leak inside his slacks. "I'm sorry, Daddy," he said, reaching for the front of the slacks.

"I know you're a good boy," Cas said, smiling once again. "Get your slacks and shoes off so I can get a good look at you."

Dean held his slacks up as he kicked the shoes off, then took a breath to gather his courage and dropped the slacks, squeezing his eyes shut as he stood there in his socks and dress shirt, his tie and jacket still draped over the chair. He squirmed a bit when the moment stretched unbearably, then he flinched as suddenly Cas was there, in his space, kissing his neck and wrapping his arms around Dean, each hand grabbing an ass cheek, pulling Dean up against him.

"Were you worried Daddy wouldn't like your panties?" Cas asked, a whisper in Dean's right ear.

Dean let out a relieved chuckle. "I wasn't sure."

"You were so brave, dropping your slacks when you were so worried," Cas said, hands caressing and cradling Dean's ass.

"So you like them, Daddy?" Dean asked, even though he could feel Cas' erection against his own.

"They're beautiful, baby boy," Cas said. "So soft and silky. What made you choose the color?"

Dean grinned. "I kinda have a thing for anything blue and pretty."

Cas pulled back and chuckled, reaching up to hold Dean's neck with both hands. "Well, I think Daddy might have to spank you anyway, but it'll be a good boy spanking and I'll leave those panties on while I smack your bottom."

Dean groaned, his knees weak just from the promises coming from Cas' mouth. "Yes, Daddy."

"Okay, bend over the desk so Daddy can get a good look at those panties," Cas said, giving Dean a little pat on his ass.

Dean shoved everything from the left side of his desk over to the right side, then pressed his chest to the cleared side, spreading his legs and looking over his shoulder at Cas.

"Like this, Daddy?" Dean said.

"Just like that," Cas said, standing back to admire the view. "So why didn't you ever tell Daddy that you liked wearing panties?"

Dean crossed his arms on the desk, then used them as a pillow for his chin. "I don't know."

"I don't like that answer," Cas said, then gave Dean a firm smack on his left ass cheek. "Try again."

"Sorry, Daddy," Dean said, squirming. "I was worried you wouldn't like them."

"And you didn't know I'd come down here today," Cas said as he ran his index finger over the lacy waist band.

"No," Dean admitted.

"You weren't going to tell me yet," Cas said, his finger tracing the crack of Dean's ass.

"No."

"Daddy still wants to be with you, no matter what you like," Cas said. "You know that, don't you?"

Dean pushed his face into his arms. "Yes," he said softly.

"Dean, look at me," Cas said.

Dean looked over his shoulder at Cas. "Yes, Daddy?"

"Tell me you know that you can tell Daddy anything and he'll still want you," Cas said.

Dean nodded. "I know, Daddy."

Cas smacked his ass. "Tell me."

Dean's throat felt a little tight, and he hesitated just long enough that Cas must've decided he wasn't going to answer at all.

"You're already getting a good boy spanking," Cas said, "but if you tell me, I'll fuck you with your panties on."

Dean hissed as his cock twitched, painfully hard. "I know Daddy still wants me no matter what I like."

"Good boy," Cas said, then put a hand on Dean's back over the dress shirt, thumb rubbing back and forth. "Relax."

Dean rested his chin on his folded arms again, smiling as Cas ran his hand over his ass, grabbing and just touching, the panties obviously something Cas was getting a kick out of.

When the first slap came, Dean just moaned, because it wasn't harsh. It was perfect. It was just enough to make his ass jiggle, and Dean suddenly wished he could see what they looked like, wished he had a mirror in his office.

And that's when he remembered he forgot to close the blinds. He turned his head and looked at one of the big windows, eyes wide. If the guys across the way had their binoculars out, they'd get a pretty good view of what was going on.

"Are they watching?" Cas asked, ever observant.

"No," Dean said, putting his chin back down on his arms.

"Not yet," Cas said, and Dean could hear the smile in his voice.

Another few slaps landed, another, and Dean could feel the wet spot on the front of the panties getting larger, the cool air on his legs, the gentle rubbing of Cas' thumb on his back. He could smell Cas' cologne and the wood of the desk beneath him.

And then Cas was gone. Dean was about to stand up when he felt Cas fingers at the waist band of his panties, pulling them down so slowly that Dean whimpered. When they were about halfway down his ass, Dean smiled as Cas placed soft kisses on each of his ass cheeks, right where the panties met his skin.

The panties came down further, and more kisses followed, then a small lick to the crack of his ass. Dean spread his legs a bit more as the panties finally slid down under the curve of his ass.

Cas spread his cheeks, then huffed a breath over his hole. Dean whimpered, pushing his ass toward Cas.

"Do you want something, little one?" Cas asked.

Dean nodded against his arms. "Yes, Daddy. Want _you_."

"What if they see us?" Cas asked. "What if they see you bent over your desk with your boss behind you, fucking you until you come in your little blue panties?"

Dean went up on his toes as Cas ran the lubed pad of his index finger over his hole. "Please, Daddy."

"Please what?" he asked as he dipped his index finger into Dean's hole just the tiniest bit.

"Please fuck me, Daddy," Dean begged, trying to push back, get more of Cas inside him.

"You're such a good boy," Cas said as he pushed his index finger into Dean. "Such a good boy for Daddy."

Dean gasped as Cas pushed a second finger in, not giving him much time to adjust to the first one. "Daddy!

"Yes, baby?" Cas said, as if he didn't have two fingers inside Dean, as if he wasn't finding Dean's prostate and rubbing over it.

"Please," Dean moaned, hips twisting back and forth as Cas played with him. "Please fuck me, Daddy."

Cas pulled his fingers out and pressed one last kiss to each of Dean's cheeks. Dean could hear Cas' clothes rustling behind him, heard the zipper, and as Cas sank into him, his cock stretching him wide open, Dean nearly sobbed with relief. Because Cas was finally inside him, Cas was filling him, and Cas going to let him come.

"Is that better?" Cas asked as he bottomed out.

Dean hissed at the stretch, Cas' two fingers not having been enough, but that was fine with Dean. He liked to feel it, liked to squirm beneath Cas as the man made him take it. Cas was all about intensity, even when it came to just getting his cock inside Dean.

"Yes, Daddy," Dean said, feeling the urge to rest his hands on the desk and push himself up, but he didn't, because Daddy had told him to bend over the desk.

"Such a good boy," Cas said as he started fucking, slowly at first until Dean adjusted, and then he was fucking him hard, the desk creaking with the force of his thrusts.

Cas changed the angle of his thrusts, and Dean let out a long whine as it let Cas' cock drag just right over Dean's prostate.

Cas chuckled. "We have an audience," he said.

Dean turned to the window, eyes wide and his jaw dropped when he saw the guys crowded around the window across the way, each of them fighting over the binoculars. Dean blushed, but it turned him on even more.

"They're watching, baby," Cas said. "Watching while I reward you for being my good little boy."

"Yes, Daddy," Dean said.

"They can't see your panties from this angle," Cas said.

Dean's breath caught in his chest, and he finally remembered to breathe when Cas wrapped his arms around Dean and turned them, still fucking Dean as he pushed him against the full-length window, Dean's panties against the glass.

"There, now they can see your pretty panties," Cas said as he reached into Dean's panties and wrapped his hand around Dean's cock.

Dean rested his forehead on the glass, his hands to either side of his head. The cleaning woman would complain about the fingerprints on the glass, but he didn't care.

"They want to see you come, little one," Cas said. "They want to see you get these pretty panties all dirty."

Dean let out a groan, so close to coming that he couldn't even speak, just pant against the glass as his cock was stroked just the way he liked it and Cas pounded into him from behind.

"Daddy!" Dean whimpered, toes curling in his socks as he came, jizz hitting the window once, twice, then getting smeared all over as Cas fucked him harder and Dean's cock was ground against the window, slippery from his release.

"My good boy," Cas said as he came inside Dean, left arm wrapped around him, holding him tight, his right hand still squeezing Dean's cock.

Cas gently pulled out of Dean, and soon Dean was chuckling as Cas used his handkerchief to wipe between his ass cheeks, cleaning him up. Cas pulled the panties up, then gave Dean's ass a little pat.

"You were a very good boy," Cas said, then kissed Dean's back. "Clean up the window so Kelly doesn't have to, and then get back to work."

"Yes, Daddy," Dean said, smiling as Cas walked out of the office, closing the door behind him.


	16. Sick of Me

**Summary for the Chapter:**

> **Anon Request:** Sam/Dean. Dean gets turned on by being taken care of, since he's always been doing the one taking care of people, but nobody knows because he has this phobia about anyone finding out, even - especially Sam. I'm thinking maybe being sick and fantasizing Sam will care take of him would turn him on the most in my headcanon, because being hurt fighting monsters is something that feels like a badge of honor, but being sick is just something his dad made him feel bad about. So, Dean is sick and feverish and therefore emotionally liable, and gets turned on by being taken care of, and Sam figures it out. And maybe Dean has a bit of an emotional breakdown on top of this because I feel like that would be a cathartic moment for him.

**Notes for the Chapter:**

>  **Warnings:** None other than Sam/Dean incest.
> 
>  **Tags for This Chapter:** Sam/Dean, sick!Dean, crying!Dean, caretaker!Sam, caretaker!kink, handjob, kissing, fluff, switching discussed

Dean hates sneezing. He hates throwing up. He hates shivering when the temperature in the room is normal for everyone else. He hates the taste of cough syrup. He hates how his nose and eyes leak constantly when he's sick.

But it's all worth it whenever Sam runs his fingers through Dean's hair, checking his temperature in a way that he thinks will fool Dean into believing he's just soothing with his touches. It's worth it when Sam jogs across the street in the pouring rain to get more cough syrup, tissues, and those crackers that settle Dean's tummy.

Sam shakes his head and kicks the door closed behind him. "I got you some of those cough drops you like," he says, reaching into the bag and pulling out a brightly-colored box.

"Tha-," Dean starts, but then a coughing fit overtakes him, and he covers his mouth while he wonders if he'll ever be able to breathe again. "Thanks, man," he says when he finally gets it under control.

Sam walks up to the nightstand by the bed Dean's sprawled out on. He's dressed in pajama bottoms and an old, worn out, black T-shirt with holes and faded stains. He's also got the blanket pulled up to his chin, because he's fucking cold.

"They had the shitty crackers you like," Sam says as he pulls out a bag of crackers.

They really _are_ shitty. Dean's tried to eat them when he's not sick and can't stand them. But for some reason when he's sick, it's the only thing he can keep down along with some ginger ale.

Sam sets a few more items on the nightstand, then pulls a six-pack of ginger ale out, opens a can, and sets it on the nightstand. The ginger ale isn't even the store brand. It's the real stuff. The expensive stuff.

Dean's mouth waters even as his cock is getting harder, and he's glad that he has a fever, because then maybe Sam won't notice the blush on his cheeks. Sam runs his fingers through Dean's hair, checking Dean's temperature, then sighs.

"I'm gonna need to wipe you down," Sam says, then turns and walks into the bathroom.

"Fuck," Dean says under his breath. "Shit, shit, shit."

He tries to think unsexy thoughts, but he can hear Sam filling the ice bucket with water, and he just knows it's not cold water. Sam wouldn't do that to him. He's filling it with room temperature water, just enough to cool him down, and it just makes Dean even harder. He pulls the T-shirt over his head and tosses it on the floor between the beds and flings the blanket off before turning onto his stomach. Maybe he can buy himself some time by letting Sam wipe down his back first.

The problem is nothing unsexy works, because this thing that Dean has, this strange thing that he's never told anyone before, that no one has ever noticed because he's managed to hide it, well, it's weird. He doesn't know why it happens. Who gets aroused when they're sick? Who the fuck likes being taken care of so much that they can't get rid of an erection?

"Dude!" Dean complains as Sam starts yanking the pajama pants down.

"Lift up," Sam says.

"No," Dean says into the pillow.

"So grumpy when you're sick," Sam says under his breath as he grabs Dean's hips, pulls him back, then quickly yanks the pajama pants down before Dean can stop him.

Sam knows how to take care of him, how to move him, knows all his tells, his insecurities, but he's never figured out Dean's dirty little secret. Dean doesn't get sick all that often, and he doesn't usually get a fever, which means stripping down to nothing isn't a common occurrence when he's sick.

Dean squeezes his eyes closed and thinks of digging graves, of half-rotted bodies and the smell as they break open the caskets to do a salt and burn. He thinks of how zombie gore just doesn't come out of their clothes, how it stinks so badly that they just have to burn the clothes. He thinks of the stench of the flowers they fell into when chasing after a witch a few weeks back.

All while Sam wipes down his back, taking care of him, making sure Dean's temperature goes down. Carefully caressing his back, his arms, his ass, his legs, and even between his toes.

Dean tries harder. Because the erection is still there. It's even worse. He brings out the big guns and imagines Pastor Jim making him sit through a sermon on sin.

"Hey!" Dean yelps as Sam flips him over. Dean looks up at Sam with wide eyes, his breath caught in his chest.

Sam chuckles. "What?" he asks, shrugging, then looks down and sees it. Dean's hard. So hard he's leaking. Sam meets his eyes again, smiling. "It's not the first time I've seen you hard. Relax, man."

Dean opens his mouth, ready to plead his case, explain that he's just horny, that the fever is making him delirious, that the full moon is affecting his dick the same way it affects the tides, that the planets are arranging and... Nothing comes out of his mouth.

"It's okay, Dean," Sam says as he wrings out the washcloth and starts with Dean's face, then moves on to his neck, wiping with that gentle efficiency Sam is capable of.

"Sorry," Dean says.

"It really doesn't bother me," Sam says.

Dean hisses as Sam wipes under his left arm, then his right. He already felt cold, and now he's shivering.

Sam wipes over his stomach, then just keeps going. He wipes down between his legs, catching the creases where a body holds most of its heat. Dean whimpers, shivering with the cold even though he knows the washcloth is damp with room-temperature water. Sam works his way down Dean's legs, then gives him a pat on the arm as he stands up.

"Torture's over," he says as he tosses the washcloth into the ice bucket. "How's your stomach?"

"S'okay," Dean mumbles, unable to meet Sam's gaze.

"I'm going to rinse out the bucket," Sam says as he heads for the bathroom. "Don't cover up while I'm in there."

"'K," Dean says, his cock twitching at the concern in Sam's voice, the way Sam is ordering him around for his own good.

He's so sick, and not just physically. He knows he's not right in the head, knows only some weirdo would get turned on by this, but he can't help it. His balls are aching, his throat hurts, his shoulders are tense and sore, he's cold, and Sam's going to come back out of the bathroom any second and Dean's still going to be hard and leaking.

Sam shouldn't have to put up with this. Where's Sam's house and white picket fence with his two point five kids, a loving wife, and a dog? No, instead he's stuck wiping his big brother down while Dean practically humps his leg just because Sam's taking care of him.

By the time Sam climbs onto the bed, scooting back until he's resting against the headboard, Dean's convinced himself he's the most disgusting pervert ever.

"You wanna watch a movie?" Sam asks.

And there it is again. Sam's concerned. He's thinking about Dean, keeping an eye on him, and Dean's eyes are burning. He can't stop himself. One minute he's shivering and the next he's trying to curl into a ball, away from Sam, away from reality.

"C'mere," Sam says, pushing him onto his back and sliding down the bed until they're level with each other, Sam turned onto his right side.

Dean squeezes his eyes shut, embarrassed as a few tears run down the sides of his face. "I'm fine," Dean says.

Sam sighs, and just as Dean's about to tell Sam to fuck off to his own fucking bed, he feels a gentle kiss on his forehead.

Dean freezes, because they're not like this. They're not soft touches and caressing and holding each other. Sam's rough and Dean doesn't like chick flick moments and Sam translates that as manhandling and fucking against the wall when they're sweaty and covered in grave dirt.

A hand wraps around his cock, and Dean lets out a noise of distress, a few more tears running down the sides of his face. Sam strokes him with slow, gentle pulls, and Dean just can't take it. The tenderness is ripping down walls he's had in place for years.

Dean turns onto his left side and shoves his face into Sam's chest so Sam can't see him. He's hiding, and if anybody has a problem with it, Dean will gladly punch them in the face.

"You think I've never noticed the tent in your boxers every time I take care of you?" Sam asks, and his voice is barely there, a whisper. He's not teasing. He's not disgusted.

Dean sniffles, hips jerking forward, fucking into Sam's hand. "Sorry," he says.

"You always seem to freak out over it," Sam says, letting out a huff of laughter. "Usually I just let you think you're hiding it from me, but I can't stand to see you this upset."

Dean doesn't know what to do. Sam's hand feels so good, and the words Sam's saying feel even better. Dean's throat feels tight, his chest is burning just as badly as his eyes, and he cringes as he lets out a sob.

"It's okay, dude," Sam says. "Everybody's got kinks, and if you would've ever asked me, I would've said I think it's hot that I turn you on by taking care of you."

"Don't fuckin' patronize me," Dean grumbles into Sam's chest, but it comes out as more of a gasp when Sam starts stroking him faster, thumb rubbing over the tip of his dick on the downstroke.

"I'm not," Sam says. "You eat up the attention when you're sick, and you never even let me hold you when you're healthy."

Dean's bottom lip trembles, because he wants that. He wants to be held, loved. He wants Sam to fuck him slowly when they have the time. Not that he doesn't like the rough sex. Of course it's fucking hot to rip each other's clothes off and fuck on the floor or in the shower or in the back seat of the Impala, fighting for dominance, fighting for who gets to top. But Dean likes to take it slow sometimes too.

Sam kisses the top of his head, then rubs his nose through Dean's hair, and Dean's not going to last much longer because this is Sam holding him, whispering to him, kissing him, and stroking his cock just right, not squeezing too hard, not pulling too fast.

When Dean comes, it's with a sob of relief. He's been hard for a long time, and letting go, letting Sam take care of him like this feels better than he ever could've imagined.

Sam keeps stroking him until Dean starts to get sensitive. They've fucked enough that Sam knows when to stop. Dean stays where he is, scared to move, scared he might break the spell they're obviously under. He doesn't want to pull away from Sam to find him laughing, ready to give Dean a hard time for being so sappy and ridiculous.

When Sam pulls away, Dean turns his face into the pillow, gritting his teeth when Sam gets off the bed. But then Sam's back, wiping him down with a washcloth. Gentle swipes while he moves Dean this way and that, getting him cooled down and cleaning him up at the same time, all traces of his tears gone, all evidence he'd come on his own belly and Sam's hand washed away.

Dean finally opens his eyes when Sam places a gentle kiss on his lips. He pushes Sam away, frowning. "Dude, I'm sick," he complains. "You're gonna get sick."

"Don't care," Sam says, taking a hold of Dean's wrists and pushing them away from his face, only to lean in and kiss Dean again.

Dean lets him, whimpering into the kiss that's so gentle, so breathtaking that Dean nearly starts crying again. Sam finally pulls away and flops down onto the bed next to Dean, smiling.

"Feel better?" Sam asks.

Dean frowns. "No. In fact I think I'm getting worse. Gonna be sick for like another week or two," he says, then pokes out his bottom lip in a pout.

Sam laughs, kisses the corner of his pouty mouth, then snuggles up next to him. "Well, then you should get your rest, because I'm not gonna let you fuck me again until you're all better."

Dean snorts. "You'll be begging for it before then."

Sam laughs again, and Dean can't help but smile at the sound. He loves it when Sam laughs, loves being the one who can make Sam happy.

"You're right," Sam says.

Dean falls asleep with a smile on his face.


	17. Pregnancy Blues

**Summary for the Chapter:**

> **Anne's Request:** (After I posted Mommy - Sam/Mpreg!Dean) Can I ask for a other wincest fic with pregnant sex (mpreg!Sam, top!Dean),please?
> 
>  **A/N:** Hey, Anne, I hope you weren't looking for penetrative sex, because it just didn't seem to happen. You've still got top!Dean. I hope you like it :)

**Notes for the Chapter:**

>  **Warnings:** Fingering of a birthing channel and pregnant!Sam/Dean incest.
> 
>  **Tags for This Chapter:** Sam/Dean, Mpreg, pregnant!Sam, Daddy!Dean, moody/hormonal!Sam, caretaker!Dean, blowjob, handjob,fluff, fingering of a birthing channel

Sam trudged out to the kitchen, opened the fridge, closed the fridge. He opened a few cupboards, closed them. He shuffled to the pantry, opened it, closed it. After letting out a huge sigh, he waddled back to the bedroom and stretched out on the bed.

He didn't know what he wanted. Oh, he knew he was horny, he was hungry, he was lonely, he was crabby, and he also knew he was ready to get his kid out. Two weeks. Only two weeks to go.

Sam spread his legs and arms out, star-fished on the bed and stared at the ceiling. He didn't know how much longer Dean would be. He went out for groceries, and sometimes Dean got distracted and took a couple hours, other times he was back in fifteen minutes. Sam hated feeling so needy, but Dean never seemed to mind.

Tears welled in Sam's eyes. Dean was so awesome, had been so wonderful throughout the entire pregnancy, through Sam's cravings and morning sickness, through his achy feet and mood swings, through his complaining and temperature intolerance. Anything below seventy-four degrees in the house was too cold, but anything over seventy-six degrees was too hot.

Sam felt useless and huge. Dean reminded him all the time that carrying their child was anything but useless, and he'd place gentle kisses on Sam's belly, on his fingers, shoulders, cheeks, neck, and that little spot that made Sam smile under his left ear. He'd tell Sam how they were going to be a family, they were going to raise their own kid, and that was because Sam was doing all the work and that Sam was beautiful, no he wasn't too huge, and that Dean could never repay Sam for what he was doing.

But Sam still felt huge. He felt inadequate. And he knew Dean was running himself ragged with working all day, then taking care of Sam all night. Sam couldn't even sleep through the night because of how uncomfortable he was, and Dean would get up with him every time.

Sam turned onto his side and looked at the clock. It was a Thursday, which meant Dean didn't have to work, but instead of resting, he was out shopping. The clock blurred, Sam's tears making the room warp around him.

"Hey, baby," Dean said from the doorway.

Sam wiped at his face and turned over. "Hey, Dean," he said, forcing a smile.

"You hungry?" Dean asked.

"Uh-huh," Sam said.

"Cottage cheese okay with you?" he asked.

Sam's diet had gotten smaller as the baby got bigger. The range of foods he could stand was down to about five items, one of which was cottage cheese.

"Yeah," Sam said.

Dean held up a container of cottage cheese, a spoon already dunked into it, the handle sticking out. "Here ya go," he said, handing the container to Sam.

Sam took it as he sat up. Or actually he tried to move, but ended up just flailing pathetically. Dean didn't hesitate to wrap his hands around Sam's upper arms and help him up.

"Sorry," Sam mumbled, looking down at his belly, his T-shirt stretched over the bulge, but not long enough to cover the underside of his belly. His sweat pants were tucked under and irritating his skin. Sam frowned, feeling like a complete invalid. 

"C'mon," Dean said, getting a better grip on him by wrapping his arms around Sam's upper chest, under his arms, and sliding him back on the bed until he was sitting against the headboard.

"Sorry," Sam said again.

But Dean was already moving him around again, lifting him enough to pull the sweats down and off. Dean knew clothes were uncomfortable, and he didn't even ask, just helped Sam.

Sam sniffled, then let out a watery chuckle when Dean pushed his shirt up and kissed his belly.

"I know you're hungry," Dean said, "so go ahead and dig in while I make you feel good."

Sam opened his mouth to ask what the fuck Dean meant, a little irritated even though he'd been smiling just a moment before, but then Dean was climbing between his legs, settling down on the bed, and sucking his cock down.

"Oh," Sam gasped, spreading his legs, his head thunking back onto the headboard. His cock had already been half hard, but the attention was making him even harder.

Dean pulled back and grinned up at him. "Eat your cottage cheese," he said, then sank down on Sam's cock again.

Sam felt his face heat up. Could he really? Could he pig out on cottage cheese while Dean was sucking him off? It sounded awesome. He really was hungry, and he felt good for the first time in about two days.

Dean rolled Sam's balls in his left hand while he bobbed on Sam's cock, not at all concerned about Sam splitting his attention between the awesome blowjob and the cottage cheese, so Sam set the container on his belly, holding it steady with one hand while he shoveled the cottage cheese into his mouth with the other.

Sam moaned, and he really couldn't tell whether he was happier about the cottage cheese or the blowjob. It didn't really matter, because Dean had was doing it all for him, and his moan of appreciation covered it all.

The fingers of Dean's right hand trailed underneath his balls, over the opening that had recently developed for Sam to give birth. Sam shivered, the hole very sensitive. Dean was extra careful whenever he touched Sam there. It was a great source of pleasure, and Dean knew it, but he also knew that being too rough didn't feel good at all, and Dean was quick to learn anything about Sam.

Sam was too busy shoving cottage cheese into his face to figure out where Dean got the lube, but a lubed finger entered his birthing channel, making him flinch. Dean didn't pull out or hesitate because Sam always flinched, not because it hurt, but because it just felt so good.

Dean gently pushed in, then slowly pulled out before repeating the process over again while still sucking Sam's cock, Sam's balls resting in his left hand.

"Dean," Sam gasped around a mouthful of cottage cheese, his eyes closing.

Dean hummed around Sam's cock as he circled his index finger, running around the rim of Sam's hole, and that was it. Sam was coming down Dean's throat, his birthing channel clenching around Dean's finger as his balls pulled up close to his body, Sam moaning the whole time around his cottage cheese.

Sam relaxed against the bed, muscles finally settling that hadn't settled since the last time Dean had made him come after a massage that was out of this world.

Dean licked him clean, then pulled his finger out of Sam's hole and sucked it clean too. Sam moaned, eyes on Dean's lips. Dean got to his knees, opened up his jeans, pulled himself out, and stroked himself while sucking his finger, eyes locked with Sam's. It didn't take long and Dean was coming on Sam's left thigh, eyes closing and mouth open as he gasped out Sam's name.

Sam frowned at the mess on his leg, and as soon as Dean realized what the frown was for, he leaned down and licked up his mess. When he straightened up again, he was smiling.

"You're so fuckin' sexy," Dean said, then leaned in and kissed the corner of Sam's mouth, licking some stray cottage cheese off Sam's face.

Sam chuckled and pushed him away. "You're gross," he said, but he didn't really mean it. He was laughing and didn't feel lonely anymore. Especially when Dean snuggled up against him and rested a hand on his belly, whispering his love into Sam's ear.


	18. The Mark of Freedom

**Summary for the Chapter:**

> **Lori's Request:** Can you do something with dark!Dean? Demon Dean or MOC Dean works too. I'd like more emphasis on how good Dean feels, how liberated he is with his new agenda, morals etc. Also, if you fit the theme of betrayal - how Sam didn't look for Dean while he was in Purgatory as the possible reason for Dean's anger- it would be perfect. So Dean stalks and claims his brother because unlike Sam, Dean needs his brother and now he's uninhibited enough to take what he always wanted. (If sex, only bottom Sam, pretty please)

**Notes for the Chapter:**

>  **Warnings:** Sam/Dean incest, non-con/rape, MOC!Dean
> 
>  **Tags for This Chapter:** Non-consensual Sex/ **rape** , Sam/Dean, incest, MOC!Dean, rough sex, some violence, anal sex/fucking, bottom!Sam, top!Dean

Sam's no match for him, and while that would've bothered Dean in the past, he doesn't give a shit, not now that all the weight has been lifted from his shoulders, all that responsibility that never amounted to anything anyway.

Dean walks into Sam's bedroom, not knocking, not hesitating, and it's so fucking fun to watch the way Sam's eyes widen, the way his lips open slightly, the way he sits up straighter on the bed, suddenly conscious of his lack of shirt and jeans in a way he never was before around Dean.

"Uhm, hey," Sam says nervously, setting his book on the bed next to him and glancing at the spot on Dean's arm, where he knows the Mark of Cain is. "What's going on?"

"Well, see, here's the thing," Dean says, holding his arms out before resting them on his hips. "I've come to realize that all the hangups I've had all my life just don't really matter."

"Okay," Sam says, nodding.

"In the grand scheme of things, who really gives a shit if my brother checks out my ass whenever I wear tight-fitting jeans?" Dean asks, grinning.

Sam's cheeks turn pink. "Dean, I didn't mean to-"

"No, Sammy, it's okay," Dean says, shaking his head. "That's exactly what I'm talking about. I've wanted to fuck your tight ass for years now, but because I always have to be responsible and you're my baby brother and all that other bullshit, I've held back."

Sam opens his mouth, but nothing comes out. He glances around the room, as if some answer will pop out at him, but then he looks back to Dean, and Dean's pleased to see there's some interest in his eyes along with the fear.

Because this new Dean isn't just devoid of morals. He's not some monster. He's just free of anything that held him back before. The shoulds and shouldn'ts just don't matter. Dean still has no desire to randomly mow people down with his car, but he doesn't have that little voice in the back of his head saying he needs to be good.

"Dean, maybe you don't want to-"

"Oh, but I do," Dean says as he pulls his shirts off over his head and drops them on the floor. "You've been mine since the day they let me hold you. You're still mine. And now I'm gonna claim what's mine."

Sam gasps, scooting back on the bed even though he's already sitting against the wall. Dean pounces, yanking Sam down the bed by his knees and getting between his legs, grinning down at Sam.

"You look adorable when you're trying to be a good boy," Dean teases, poking at Sam's belly.

"Dean, c'mon," Sam says, trying to sit up, putting a hand on Dean's chest, but not pushing. "You don't wanna do this."

"No, I really do," Dean says, fingers grazing the slit of Sam's boxers.

"Dude, stop!" Sam says, squirming and pushing at his hands.

"You were so much more open to new things when you didn't have that pesky soul," Dean says, chuckling. "At least when you were soulless, you didn't make any excuses for doing shitty things like leaving your brother in purgatory."

Sam freezes, his eyes going impossibly wide. "I-I thought you were okay with that. I moved on. Like you told me to do!"

"I only said I was okay with it because you would've been all pouty about it otherwise," Dean says, reaching into the slit of Sam's boxers and wrapping his fingers around Sam's cock.

Sam whimpers, closing his eyes, and very obviously not that upset with the stimulation his cock is getting. It's been too long since anybody touched it, and Dean finds it amusing that Sam is so easy.

"Stop!" Sam says, eyes opening and his hands more forceful as he pushes at Dean's shoulders.

"Oh, I don't think so," Dean says. "I'm already hard, and I wanna see just how tight your hole is."

Sam's had enough, and Dean can see when his little brother finally realizes this isn't funny anymore.

"Dean, stop!" Sam says, the fingers of his right hand jabbing out to catch Dean in the throat.

Dean easily stops him by grabbing his wrist and twisting. Sam yelps, and Dean lets go, chuckling at the wounded expression on Sam's face.

"Don't fight me and you won't get hurt," Dean says flippantly.

Sam flails, trying to get a punch in while simultaneously trying to roll them, to get Dean off. Dean moves with it, lets Sam get a punch in so he can start yanking at Sam's boxers. The sound of material shredding is loud in the room, as is Sam's yelp of pain, most likely from the material catching his balls, and Dean pulls until the boxers give and come off, the shreds lost in the folds of the blanket beneath them.

"Wait!" Sam says, squirming and panting. "Stop! Dean, you don't wanna do this! Stop!"

"Come up with a better line, baby brother," Dean says as he reaches under the pillow, where he knows Sam's bottle of lube is. They grew up in close quarters, know way too much about each other, and soon enough Dean's flicking the top open.

"Dean, please stop!" Sam yells as Dean braces his right forearm over Sam's chest and shoves his hand between them to squirt lube directly on Sam's hole.

Dean tosses the lube, then shoves three fingers into Sam's hole. "You're not as tight as I thought you'd be," Dean says, then chuckles in Sam's face.

"You know I fuck guys," Sam hisses, reaching up to choke Dean.

Dean grabs his balls and squeezes, Sam's hands loosening immediately. "I wouldn't suggest trying to knock me out. You might kill me, and this right here will look like nothin' once I come back."

Sam lets out a noise of distress as Dean shifts. He tries to hit Dean's shoulders, his chest, even his face, but Dean just chuckles and shoves his cock in Sam's hole.

"No!" Sam yells, his entire body tensing as Dean bottoms out.

"You know you wanted it, Sammy," Dean says as he starts thrusting in and out of Sam. "Think of this as a free pass. You get laid, you get to see what I'm like in bed, and when it's all over, if you wanna go again, you just ask. I'm not hard to get along with."

Sam squeezes his eyes shut and grits his teeth, his fingers digging into Dean's forearms. Dean can feel something inside him shift, something that feels very right, because as soon as he was inside Sam, as soon as his baby brother was truly his, Dean felt complete. The truth was that Sam never needed Dean, but Dean needed Sam, and now he had him.

"You wanna come too?" Dean asks, then bites down on Sam's left shoulder.

"Fuck!" Sam yelps, twisting away from the pain.

"Aww, but I thought you liked biting," Dean sing-songs.

"Get off of me," Sam says, voice low. "You got your way, now get off."

"I'm almost there," Dean says, grinning down at Sam when Sam opens his eyes to glare at Dean. "You sure you don't wanna come too? I don't mind giving you a little hand action."

"No," Sam says, voice tightly controlled.

"Your loss," Dean says, then starts fucking into Sam so hard the bed squeaks and Sam's body tenses up. "But I think you're missing out on an awesome opportunity. I know you've had a thing for me ever since you were a teenager, and before I had this sense of freedom, I bet you never even noticed. So take advantage of it now, Sammy."

Dean can see the realization in Sam's eyes, and he feels a sense of victory, because Sam never knew that Dean knew, and Sam never knew Dean felt the same way. But it didn't matter, because now Dean was taking something that wasn't offered, and any fun in the future would have to be taken instead of given. That was okay with Dean. The loss of all those hang-ups was the best thing that ever happened to him.

"I'm gonna come inside you, little brother," Dean says, looking Sam in the eye, watching as that last bit of hope dies. "Oh, fuck, yeah," he groans, writhing all over Sam instead of pounding into him as he fills Sam with his release. "You feel that? It means you're mine. Every part of you is mine."

Sam stares off over Dean's right shoulder, lips thinned out in an almost-pout, brow furrowed with anger and pain. Dean pulls out and sits back on his heels.

"You really should've let me at least give you a hand job," Dean says, as if he's disappointed. "You would've had much more fun," he says as he pats Sam's left inner thigh.

Sam doesn't move or acknowledge him, doesn't move, and his breathing remains shallow, controlled.

Dean shrugs as he gets off the bed. "You hungry? I'm hungry. Stay here and I'll go get us something to eat. I'll make your sandwich just the way you like it."

He walks out of Sam's bedroom, his jeans still open, cock still hanging out. He feels good, right, complete in a way he hasn't for decades. But he's also hungry, so he heads for the kitchen.


	19. I'm Here

**Summary for the Chapter:**

> **sixbucksandwingless' Request:** I would really love it if you wrote a fic with dom!Cas and sub!Dean, in canon verse. Dean comes home after a rough hunt and needs Cas to take him out of his head for a while. Cas uses his grace for bondage and whatever else you can think of. And please include lots of loving aftercare. Could you include begging, orgasm denial(maybe with a cock ring?), and spanking? You can still have Cas use his grace to tie Dean up with, or if you think it would work better using actual rope or handcuffs, that's okay too :)
> 
>  **A/N:** This was more fluffy than I had originally intended, but Dean really needed some love, which means by the time he would’ve needed aftercare, he’s gotten everything he’s needed.

**Notes for the Chapter:**

>  **Warnings:** None for this chapter, everything's consensual.
> 
>  **Tags for This Chapter:** Dean/Castiel, dom!Cas/sub!Dean, established relationship, flogging, grace bondage, mild CBT, blowjob, begging, orgasm denial, prostate massage, fluff

Cas can always tell, just by the look on Dean's face. He doesn't need to shove his way into Dean's head, and Dean doesn't like that anyway. The ride back to the bunker is quiet; the sound of the road under the Impala's tires, the honk of a horn as someone cuts off someone else on the highway, the crickets chirping as they pull up outside the bunker.

Dean heads straight inside, and Cas follows him, leaving Sam to make his way in and take care of the weapons like he said he was going to. By the time Cas gets to Dean's bedroom, Dean's already kneeling on the floor, arms behind his back, knees spread, head slightly bowed. He's still in his jeans, shirts, socks, and boots, but the jacket is draped over the chair in the corner.

Cas can see the tension in Dean's body, the tight shoulders, the furrowed brow of someone who doesn't like what they just had to do, but they knew it was necessary. Dean carries those weights, and this is the healthiest way they've come up with for lifting them off his shoulders.

Dean licks his lips as Cas closes the door. His eyes track Cas, watching as Cas takes his coat off, his tie, kicks off his shoes, and rolls up his sleeves. The belt comes off too because the buckle leaving a mark on Dean's leg once had been the first and last time Cas had worn it while they were playing.

"What do you want?" Cas asks. Of course he knows, but it's all part of the game, part of what pulls Dean out of the headspace he puts himself in after rough hunts.

Dean doesn't answer, so Cas makes a slight adjustment in his plans. It isn't every time that Dean gets like this. There are times they play in their regular sex life, and there are times they use it as stress relief, both mild and severe. Dean having resorted to keeping his mouth shut means a little more severe.

"Look at me," Cas says, standing in front of Dean.

Dean obeys, and Cas can see the anger in those beautiful green eyes, the pain. There's also defiance and a challenge. That's okay. Cas doesn't have a problem with that.

"Tell me what you want or I'm going to start with your least favorite and work my way up," Cas threatens.

Dean looks down at the floor again. "Don't," he says softly, teeth clenched.

"Then tell me what you want," Cas says. Dean hates puppy role play, and Cas has a butt plug with an adorable little tail waiting in their toy box that he can pull out if Dean doesn't answer.

Dean meets his eyes again, a little less defiance, but the pain is still there. "I want to feel... you."

It's halting and it seems as if Dean is forcing it out, but Cas knows exactly what he means, and he smiles as Dean gasps, eyes fluttering closed as his body jerks. Cas stands back, his grace flowing over Dean, wrapping around his wrists, his ankles, his cock, holding him right where Cas wants him, and Dean's cock is already responding.

"Yeah," Dean whispers.

Dean's life has never been full of control, and he's scrabbled for what little he could get, but when Cas walked in and turned his life upside down, Dean found a creature capable of controlling every single aspect of him, who was larger than the room they were in, stronger than Dean could imagine, and Dean was comforted by the fact that all the strength, all the grace Cas had could be used to hold him down, treat him roughly or with tender care, and all the while Dean could relax because Cas loved him and would never damage him. Dean could let go.

Cas crouches in front of Dean and lifts his chin with a finger. "Stinging or thudding?" he asks, because he always gives Dean choices. Dean doesn't get many of those, but Cas is different.

"Thud," Dean says, and Cas nods, his fingers running over Dean's neck as he stands and walks to their closet.

Cas pulls out Dean's favorite flogger. It doesn't give the same thud that a paddle does, but Dean loves it, and Cas feels like watching Dean writhe with pleasure. By the time he turns back around, he's stretched Dean out, standing in the middle of the room, spread eagle with only Cas' grace holding him there.

Dean's panting, mouth open as Cas walks around to the front of him. He lets Dean see the flogger, running the tips of the suede over his own hand and fingers, Dean's eyes tracking the movement of the falls as they gracefully move.

"I'm going to start with five," Cas says, then waits for Dean to nod before walking around behind Dean. He unbuttons and unzips the jeans and pulls both the jeans and underwear down to Dean's ankles.

A gentle flick of the flogger teases Dean's ass, making the shirt tail flutter. The next swing is aimed between Dean's legs, keeping it far enough back that it tickles the crack of his ass, his inner thighs, and just barely touches his balls.

Dean lets out a groan, body already relaxing, so Cas flicks again, this time over Dean's left ass cheek, then his right before once more going between his legs.

"Five more, heavier," Cas says. He always works in groups of five, always tells Dean exactly what he's doing. Not only is it part of the game, but it makes for a calmer Dean, because he always knows what to expect, is never scared of Cas or jumpy.

Cas pulls his arm back, then uses a little more strength, coming down on the crease between Dean's right ass cheek and his thigh, letting the falls wrap around the side of his leg. He isn't moving fast enough to hurt, just enough to sensitize the skin. He repeats with Dean's left side, back to his right, then his left again before finishing the set with the same strength across both ass cheeks.

Dean's breathing has calmed down. He isn't panting. He's obviously aroused and excited, but he's already settled in for the play time.

"How many sets have I done so far?" Cas asks.

"Two," Dean replies.

Keeping Dean out of subspace for as long as possible is Cas' goal. Most people want to reach it as quickly as possible, and Dean had fought him on it the first few times, but when he realized Cas wasn't going to budge on it, he went with the flow and loved it. Everything was more intense, and when he finally released everything and just let Cas take over, when Cas let him come, that was his high, and he'd stay there for a long time, shoved in so hard and so fast that it was like nothing Dean had experienced before.

"Five more, heavier, underhanded," Cas says.

"Okay," Dean says, nodding.

Cas pulls back, then brings his hand up more quickly than he had the other times, hitting the back of Dean's right thigh. Dean's breathing hitches, and as Cas brings the flogger up and hits the back of his left thigh, Dean whimpers. It isn't because of the pain. It doesn't even really hurt yet. It's because Dean is enjoying himself, slowly letting go of the day.

The right thigh is hit again, then the left before Cas hits both of Dean's ass cheeks with the last stroke. Dean doesn't flinch when Cas wraps his arms around him from behind and kisses his right shoulder through the shirts. Cas pulls the falls over Dean's cock while running his left hand up under his shirt, across his belly.

"Are you hard for me?" Cas asks.

"Yes," Dean says, voice a little breathy.

Cas can't praise him yet. Dean won't accept it until he'd relaxed more, so Cas kisses him again and pulls back. "Five more, and I'm going to make it sting."

"Okay," Dean says.

Dean's right outer thigh takes the first stroke, but instead of flinching, Dean's body relaxes just a little more. The stroke on his left outer thigh has him whimpering again. Cas keeps the same pace, the same amount of time between strokes, and the third hit lands across both ass cheeks.

"Cas," Dean moans.

"Yes, Dean?" Cas says, smiling because Dean can't see him. He brings the flogger down again on Dean's ass.

"Need more," Dean says.

"We'll get there," Cas says, trailing the handle over the crack of Dean's ass. "How many sets have I used on you so far?"

"Four," Dean says.

"Five more strokes, and these will hurt," Cas says.

Dean doesn't brace himself. He lets Cas hold him up with his grace, trusting Cas to be there for him. The first strike is over Dean's right ass cheek, the falls wrapping and stinging his outer hip. Dean hisses, but doesn't flinch away, and Cas hears another hiss as he does the same to Dean's left ass cheek. Two more strikes over the meaty part of Dean's ass, a gasp out of Dean each time, and then Cas is running his hand gently over Dean's ass cheeks.

"How many sets?" Cas asks.

"Five," Dean says.

"Good boy," Cas says.

Dean tenses a little, but he doesn't say anything about it, so they're getting closer to that place Cas is taking them.

"Five more, medium, on your back," Cas says as he makes Dean's shirts disappear.

Dean squirms a little, but doesn't try to get away. Cas raises the flogger, then snaps across Dean's right upper back, his left, his right, his left, then hit the middle. He wraps his arms around Dean from behind again, kissing his bare shoulder and letting the falls graze Dean's cock.

"One more set with the flogger," Cas says. "I'm going to spread your legs. I want you to feel it everywhere."

"Okay," Dean says, preparing himself, but not scared.

Cas pulls with his grace, spreading Dean's legs more, then steps back. He brings the flogger down on Dean's left inner thigh, letting the tips barely touch Dean's balls. Dean hisses, but Cas is already moving, coming around Dean's front and catching him across the chest. Dean winces, keeping his chin raised high so Cas doesn't accidentally hit his face with the falls, then Cas walks around and lands a stroke on Dean's left outer thigh.

"Ah," Dean whimpers, cringing a little at the pain.

Cas walks around behind him and brings the flogger down over Dean's right inner thigh, again barely touching his balls with the tips of the falls, but there is more force in the stroke. Dean goes up on his toes, gasping. The final stroke comes down on both ass cheeks, and Dean lets out another gasp.

"Good boy," Cas says, a gentle hand trailing over Dean's pink ass cheeks. "Is there anything else you want?"

Dean nods, and Cas runs the tips of his fingers over Dean's back, his sides, and walks around to the front of Dean, wrapping his fingers around Dean's cock.

"Tell me," Cas says.

Dean's looking at the floor, which means he isn't quite ready yet. "More," he says.

"More what?" Cas says, keeping his voice soft, keeping the mood of the room level.

"Just...," Dean says, then shakes his head.

Cas kisses his shoulder again. Dean needs time to let go of everything, and if he isn't ready yet, that's okay. Cas tosses the flogger onto the dresser and walks up to Dean, trailing his index finger over Dean's chest, down to his belly, around the soft skin, and finally wraps his hand around Dean's balls.

That gets Dean's attention, and he lifts his chin to look Cas in the eye. "I'm paying attention," Dean says, worried but not scared.

"I want your full attention," Cas says, gently squeezing. "You're here with me."

"I know," Dean says, nodding. "Sorry."

"It's okay," Cas says, giving Dean a small smile. "You're being very good for me."

Dean nods. "Okay."

Cas wraps his left hand around Dean's cock, thumb just under the head, massaging the bundle of nerves. Dean's mouth opens slightly, eyelids drooping some.

"I'm going to squeeze, and you're going to stay still for me," Cas says.

Dean nods. "Okay, Cas," he says.

Cas squeezes, not hard enough to bruise, but enough to make Dean freeze, his mouth open, eyes locked with Cas' as he holds his breath. Cas keeps massaging just under the head, the sensations warring with one another in Dean's body, and just as Dean lets out a little squeak, Cas eases up.

"I'm paying attention," Dean says, voice higher than before. "I'm here."

"Almost," Cas says, tilting his head, "but not quite."

"Fuck," Dean breathes, then grunts as Cas squeezes again.

Cas goes to his knees gracefully, hands still wrapped around Dean's sensitive parts, eyes still focused on Dean's. "When you know what you want, tell me."

Dean gasps as Cas licks the underside of his cock, then sucks on the head, still squeezing Dean's balls. "I'm here! Cas, I'm here. I swear. I-I wanna come. I wanna be good for you, and I wanna come. Wanna be good for you," he says, voice trailing off into a whisper.

Cas smiles up at him as he pulls away from Dean's cock. "You _are_ good for me. It's part of why I love you so much," he says, watching carefully as Dean can't keep the eye contact because of the praise. "I love that you're so passionate and caring," he says as he eases the pressure on Dean's balls. "I love that you want to make the world a better place. I love that you see me as more than a vessel, more than a being of light, more than I was created for. I love that you call me on my shit."

Dean meets his eyes again, letting out a huff of laughter. That's what Cas has been waiting for. That first break in Dean's resistance is always the hardest. Cas rolls Dean's balls with his right hand while he still massages that bundle of nerves. Dean's cock is leaking, so he sticks out his tongue and licks the tip, enjoying the moan that comes from Dean.

"I've seen every part of you," Cas says, pleased when Dean doesn't look away. "And I love all of it."

Cas can see Dean struggling to keep the eye contact, but it's getting easier now that Dean has started to give in, to let the praise in, to let Cas make him feel good. Dean whimpers as Cas starts stroking his cock with his left hand, his right squeezing Dean's balls rhythmically, just enough to hurt.

"What do you want?" Cas asks again.

Dean winces. "I wanna forget," he says, voice more confident.

Cas nods. It was the answer he was looking for. "What else do you want, baby?"

Dean's brow furrows even as his thighs tense, the stimulation to his cock and balls becoming much more pleasure than pain. Cas strokes faster, then leans in and kisses Dean's lower belly, nose brushing against the skin. Dean's close to coming already, so he strokes faster.

"Cas," Dean gasps. "I'm gonna come. Can I come?"

"Not yet," Cas says, lips grazing the skin of Dean's belly.

"Ah, Cas, c'mon," Dean says through clenched teeth.

A quick squeeze to the base of Dean's cock at the same time as he squeezes Dean's balls is enough to push Dean back from the edge. Dean lets out a whine of frustration.

"What do you want?" Cas asks.

Dean chuckles, his body more loose, more relaxed compared to when they first walked into the room. Cas always loves seeing him like this. That odd period of time between Dean with his walls up and Dean with his walls down. It's something Cas doesn't grow tired of.

"Wanna see you," Dean says.

Cas stands up, hands still wrapped around Dean's cock and balls. Suddenly his clothes are folded and sitting atop the dresser, next to the flogger. Dean looks down at his soft cock, always amazed, because in Dean's head, sex and nudity is always erotic, always exciting, and always something that means orgasms. It doesn't mean that for Cas, and it's as if Dean has to see it for himself every time, to remind himself or maybe just to know that this is Cas here with him and not something wearing his face.

"Better?" Cas asks.

Dean nods. "Yeah."

Cas knows Dean inside and out, and to have a partner that's there for him, who isn't in it for the sexual pleasure is something Dean's never experienced before. He's struggled his entire life being the pretty one, the hot one, the one who makes panties disintegrate with just one look, the one who is good for some short-term fun, the one they can leave behind.

Dean craves the attention, but what he wants even more is to know that he's loved for more than his body, and he gets that with Cas. There are no ulterior motives, no objectifying. Cas gives that to him.

"I'm going to put you on the bed now," Cas says, and as soon as Dean nods, Cas lets go of Dean's cock and balls, wrapping his arms around Dean's middle, carrying him over to the bed.

He hears Dean chuckle and smiles himself as he lowers Dean to the bed and climbs on after him, using his grace once again to pin Dean's limbs out, spread eagle on the bed. Cas wants to see all of him, and now that Dean isn't hiding as much anymore, Cas can see it all.

Cas wraps a small band of his grace around Dean's cock, grinning when Dean whines. "I said you can't come yet," Cas says.

Dean pouts at him, so Cas leans down and kisses the pouty lips, making Dean smile when he runs his fingers over Dean's sides. He pulls back just enough to look Dean in the eye.

"What do you want?" he whispers.

"You," Dean says, then gasps as Cas wraps his left hand around his cock again.

"I'm right here," Cas says, echoing Dean's words from earlier, a reassurance and a promise.

Cas gets to his knees between Dean's legs and rubs his right index finger and thumb together, manifesting some lube. Dean watches him closely, his cock twitching in Cas' left hand.

"You can come when you've figured out how to ask," Cas says as he pushes two fingers into Dean's hole.

Dean grimaces at the intrusion, but doesn't shy away. He likes to feel Cas even if sometimes it's not easy to take. "Please?" he asks, giving Cas an adorable smile.

Cas chuckles. "That was very nice, but no."

"Aww," Dean complains. "Pretty please?"

Cas finds Dean's prostate and starts massaging with two fingers while stroking Dean with his other hand. "No. You can do better than that."

Dean groans, legs spreading wider and his hips coming up off the bed a little. "Mmm, yeah, like that," he says, eyes fluttering closed.

"You'd better come up with a better line," Cas warns, not letting Dean get lost in his own head.

Dean smiles, eyes still closed. "Bossy," he says without any real venom.

"I'm also the one who decides whether you get to come or not," Cas says.

Dean looks up at him. "But I'm adorable! Of course you're going to let me come!" he says, cocky attitude and a relaxed way about him that warms Cas.

Cas uses his thumb on Dean's taint, massaging his prostate from inside and out, watching as Dean bites his bottom lip and pulls on the restraints holding him down, back arching.

"Okay, please," Dean says, voice strained. "Please let me come, Cas. Please!"

"Better," Cas says, nodding.

"Better?" Dean says, frowning at him. "Just better? But I said please and I was polite and-ah!" he yelps as Cas presses hard on his prostate from the inside.

Dean's cock leaks more precome as he writhes on the bed. Cas stops stroking his cock and just uses his thumb again on that spot under the head of Dean's cock, small circles that will drive Dean insane.

"Please!" Dean says as he lifts his head up off the pillow and gives Cas his most sincere look. "Please let me come. Please. I really wanna come. Please, Cas. Please!"

"Almost," Cas says, fingers moving faster inside Dean. He leans down and sucks one of Dean's balls into his mouth.

"Oh, fuck!" Dean nearly wails. "Okay, okay. Begging. You want begging and, ah, fuck. Cas, please. Please let me come. I wanna know I've been good for you, and-ahfuckyeah, I wanna. I-ah. Please! Please let me come! Please, Cas! Please! Please!"

Cas lets go of the band surrounding the base of Dean's cock and lets Dean's sac fall out of his mouth. "You may come."

Dean comes so hard he screams, back arching to the point where Cas decides to give him a neck massage later because of the muscle pull. He's fucking up into nothing, because Castiel is still just slowly rubbing that bundle of nerves, still massaging Dean's prostate, and he eases up as Dean's body flops back down onto the bed, boneless and sated, a lopsided grin on his face.

Cas lets go of Dean, all his grace pulling back, and cleans himself and Dean as he pulls his fingers out of Dean's hole. He stretches out next to Dean, smiling when Dean turns and gloms onto him before he's even settled. Cas pulls the blanket over them and lets Dean get as close as he wants, which rivals what an octopus might do if given the chance.

"Thanks, Cas," Dean mumbles into Cas' chest. "Love you."

"I love you too, Dean," Cas says as he runs his fingers through Dean's hair, then kisses the top of his head.

"You make me feel good," Dean says, voice so soft that Cas wouldn't have heard it if it wasn't for his super-human hearing.

"You deserve it," Cas says, closing his eyes with a smile on his face because Dean's walls are all down, he's accepting the praise, and he's relaxed, happy, and content.

All Dean needs to know is someone will still love him after seeing the ugliest parts of him. Cas can give that to him, because Dean's got the brightest soul of anyone he's ever seen, and he means every bit when he tells Dean he deserves it.


	20. Rough Ride

**Summary for the Chapter:**

> **Anon Request:** Can I ask for wincestiel fic where Sam and Cas wants distract Dean from the burden of the Mark and there no better way than some kinky sex...(sub-bottom!Sam, dom-top!Dean, anal), please?

**Notes for the Chapter:**

>  **Warnings:** This is all technically consensual, but I'm labeling it as **dub-con** because it's rough and MoC!Dean doesn't stop to see if everybody's on board with the sex. He can cause Sam and Cas pain, but both Sam and Cas consent and even enjoy rough sex. There's a scene that is very rough and borders on **very dub-con** , but still Dean doesn't get the chance to go through with it before Cas and Sam are on board.
> 
>  **Tags for This Chapter:** Sam/Dean/Castiel, MoC!Dean, Wincestiel, established relationship, rough sex, dub-con (read the warning below*), anal sex, oral sex, sex in a semi-public place, manhandling, object insertion, D/s, rimming, clothed sex, slight brother/incest kink, threesome, jizz as lube, bareback sex, double penetration (two holes), tickling, frottage, comeplay, dirty talk, teasing, facefucking

"Cas," Sam said, nodding toward Dean when Cas glanced his way.

Dean was staring. That glazed-eyed look he seemed to get when an urge was taking over. When the Mark pulled at him. When he forgets to fight. They were in the library doing research, and all was well, but Dean has always hated research, and Sam should've known.

Dean didn't even notice Cas sliding down under the table and crawling between Dean's legs. He gasped when Cas started unbuttoning the jeans, and Sam grinned, going back to his research while Cas sucked Dean off.

*

They didn't realize it right away. They were busy and shit was happening and life was a fuck-up of epic proportions one minute and dull as watching paint dry the next. There was no in between for hunters.

So when Dean shoved Cas up against the wall and fucked into him so hard Cas cried out in pain, Sam was surprised. He tried to help, but Dean was gone. Eyes cold and teeth sharp as he practically gnawed on Cas' neck, Cas' face smashed against the wall as he tried to tell Sam he was okay, not to get between them in case Dean got pissed.

Sam was freaked out. He didn't know what to do. Cas was willing. He always was. But Dean was never rough with Cas. He treated him like something special, and Sam didn't know what would happen to them if this was the new Dean.

But then Dean sighed, wrapped his arms around Cas, started to kiss his neck instead of bite, and his hips slowed, his thrusts more gentle. He wasn't just fucking Cas anymore, but rather holding someone he loved.

Cas seemed more surprised by that than the rough fucking, and when he and Cas shared a look, it was because they both understood they'd found the key to saving Dean. The key to keeping the Dean they knew and loved even with the Mark of Cain on his arm and in his head.

*

Sam woke to someone climbing onto his bed, but instead of being startled, he smiled into the pillow. Dean pushed him onto his stomach, hands firm and rough, and soon he was yanking Sam's boxers down. Sam wasn't scared. Not anymore. Dean could control himself much more easily once they all decided to work with what they had and run with it.

Dean didn't say anything, but Sam sure as Hell did.

"Fuck yeah!" Sam moaned into the pillow as Dean spread his cheeks and licked his hole.

Dean was always rough when it started. He took what he wanted and always had a plan in his head, an itinerary of sorts for how everything would go. As Sam writhed on the bed, gasping and pushing his ass back against Dean's face, he let go, let Dean position him how he wanted, didn't fight, and didn't try to talk to him.

And then everything came down a few notches. The real Dean was back, his hands gentle, the tongue in Sam's ass not as urgent, and by the time Dean pushed his cock into Sam's well-prepared hole, it was the real Dean again, making sure Sam got off too and kissing him as they came within seconds of each other.

*

Cas and Sam weren't delicate little flowers. They could handle it. They'd been through a lot in their lives, and getting shoved around some wasn't just tolerable, it was fucking hot.

The Dean who came at them with snarls and dark eyes and rough hands was exciting and fun. Sure it hurt at times, but Dean had always been a very giving lover. Which wasn't a bad thing, but every once in a while a guy needed some rough sex, and Dean wouldn't do it. Not if his eyes were green and he said their name like a prayer as he held them.

Sam walked into the kitchen and smiled as he saw Cas getting fucked over the long stainless steel table. His jeans and underwear were bunched at his ankles, boots still on, and Dean's right hand was fisted in the back of Cas' shirt, shoved up to Cas' neck and holding him down.

Cas was whimpering and gasping, but he sure as Hell wasn't trying to get away. Dean hadn't even bothered getting any of his own clothes off. He'd just unzipped, pulled it out, and shoved it into Cas, eyes dark, teeth bared as he fucked Cas hard enough the table would've moved had it not been bolted to the floor.

Sam loved to watch almost more than he loved participating, because the change in Dean was so dramatic, so impressive, and he couldn't always see it if his face was smashed into something.

"Mmm, Cas, yeah," Dean moaned, his thrusts slowing as he leaned down and kissed the exposed skin of Cas' back. "So good for me."

*

It was a little scary to take Dean on hunts. He'd tolerate people for the most part, but if someone wasn't being cooperative or they were just plain annoying, Dean would get antsy.

"I don't know what you're talking about," the man said. "I've never had any problems with the neighbors, and frankly I don't think the three of you are federal agents, so you really should leave."

"You want to know what I think?" Dean said, taking two steps toward the man.

Sam grabbed Dean by the arm and hauled him out of the house, leaving Cas behind to make excuses.

"Where are we goin', Sammy?" Dean asked with a grin on his face.

"To the car," Sam said, "so you can fuck me."

"Ooh, I like that plan," Dean said, "but I was just about to get that guy to give us some info."

"Yeah, well, I'd rather you fuck me," Sam said, opening the back door and climbing in.

Dean stood back, smirking at him. "You sure you don't want more info out of him? Because I'll get it for you."

Sam hurried to get his slacks and boxers down around his ankles. "C'mon. This'll be more fun."

"I don't know," Dean said, shrugging. "I haven't shoved anybody around in a while. And he looked like he'd really whine and cry a lot if I hurt him."

Sam grabbed the lube from the foot well and squeezed a generous amount onto his fingers, kicking off his shoes at the same time. The shoes, slacks, and boxers slid off the seat and into the foot well and Sam spread his legs, one foot on the back of the front seat, the other on the ceiling near the back window.

"So you don't wanna fuck me?" Sam asked, a challenge in his tone of voice that he knew would get to Dean. He reached down and shoved two fingers into his own hole, lifting his ass off the seat and giving Dean a show.

"Well, when you put it like that," Dean said, shrugging off his jacket and dropping it on the ground. "You lookin' for a good fuck?"

"Yeah," Sam said. "Want you to fuck me hard."

Dean opened his slacks and pulled out his hard cock. It was a good thing the neighborhood was off the beaten path, only a few houses within the five-mile radius around the man's house, lots of trees to keep anyone from freaking out and calling the police.

Sam jacked his own cock, the remaining lube on his fingers more than enough as Dean climbed in and fucked into him with one long push. Sam groaned, eyes fluttering closed as his head thunked back on the door. Dean fucked him hard, and Sam gasped, his back arching as his brother's thrusts squished him against the door, his neck at an odd angle.

As he looked up at Dean, he saw the moment his brother was back. The real Dean, staring down at him with soft eyes, green and loving and warm. Dean smiled, spreading himself out on Sam and lazily fucking into him as he wrapped his arms around Sam and nuzzled at his neck.

"Sammy," Dean whispered, and it was all Dean.

Even just a whisper and Sam could tell who it was fucking him, and it wasn't the same man who had nearly torn apart the guy they were interviewing. This was his brother.

*

Sam barely flinched as cold steel suddenly pressed against his neck, a presence behind him that could only be Dean. He held still, didn't move in the chair, his sandwich forgotten on the plate in front of him.

The knife scraped along his chin, and Sam could barely breathe, his cock twitching in his jeans. He couldn't hear Dean behind him, couldn't feel anything but the knife against his skin and that sixth sense he had about where Dean was at all times.

"Open up," Dean said, voice rough with disuse, as if he'd been sleeping and woke up horny, ready to fight or fuck. Or more likely both.

Sam opened his mouth, shivering when Dean pushed the handle of the knife into his mouth.

"It's all the lube you're gonna get," Dean whispered, lips brushing against Sam's ear.

Sam squeaked around the blade, the mental picture of what Dean was promising so fucking hot that he couldn't control himself. He tried to work up some spit, and inwardly cursed himself for being so turned on that his mouth was going dry.

The knife went deeper, and soon he was gagging. If there hadn't been a knife in his mouth, he would've thanked Dean for the excess spit his mouth produced because of the gagging. Dean let him gag a couple more times, then pulled the knife out.

"Jeans down, ass up over the table," Dean said. "One. Two."

Sam scrambled up and nearly ripped the jeans down. The last time he'd waited until the count of three, Dean had sliced up a perfectly good pair of jeans, so Sam wasn't going to push it.

"That's my boy," Dean said with a low chuckle as Sam draped himself over the edge of the table. "Now you'd better keep your voice down. Because if Cas hears you and comes in, I'm gonna make you watch while I fuck his ass first."

Sam couldn't speak. He almost couldn't breathe. His cock was going to fall off if Dean didn't stop it with the threats and demands and gravely voice. Sam whimpered as Dean spread his cheeks and spit on his hole.

Dean chuckled. "Such a slut for it," he said. "And still wet from earlier."

Sam felt his cheeks flush. He hadn't bothered to clean up after Dean had fucked him that morning. He liked leaking all day long, and Dean knew it. Had teased him about it. But Sam still did it.

Dean didn't bother preparing him. His hole was already lubed and a bit loose from earlier, so Dean held him open with his left hand and pushed the handle of the blade into Sam's hole with the other.

Sam gasped, the sensation strange and not really all that pleasant, but the naughty factor made it hotter than Hell. Sam tilted his ass up, ready for whatever Dean wanted to do to him.

"Feel it inside there?" Dean asked as he wiggled the handle back and forth.

"Ah!" Sam yelped, the sensation nearly overwhelming. "Fuck yeah!"

"Maybe I'll turn it around," Dean said nonchalantly. As if he wasn't suggesting shoving a sharp blade up Sam's ass.

Sam whimpered, but not because he was scared. This new Dean, this one with the Mark on his arm wasn't brutal and savage for no reason. Sure, he got rough and had fun, but deep down he still had Dean's morals, and the only time things went sideways was when Dean lost his focus, his control. Which meant Sam wasn't worried about Dean following through on the threat, and soon enough he'd have Sam coming so hard enough Cas would likely come running just from the screams of pleasure.

"Ah, fuck, Dean!" Sam cried out as Dean wiggled the handle again.

"Don't come," Dean growled. "If you come, I'm gonna make you walk around all day with this thing shoved up your ass. You're gonna have to hold onto it all day. Clenching it in this sloppy hole."

Sam squeezed his eyes shut, trying to think unsexy thoughts as Dean fucked him with the knife. "Dean!" he yelled, almost losing it all over the floor.

"You okay?" Cas asked from the doorway.

"Oh, fuck, Cas, no!" Sam whined, then shook his head when Cas hurried to him. "No, I mean I'm okay. I'm fine."

"He's upset because now he doesn't get to come until I fuck you," Dean said, grabbing Sam by the hair and pulling him up. "Hold onto it until I'm done with angel-boy over here," he said in Sam's ear.

Sam gasped as suddenly Dean wasn't behind him anymore, the knife heavy and already falling out. Sam reached back and pushed it up inside again, trying to clench around it.

"No hands!" Dean said as he turned to Cas and yanked him close.

Sam whimpered, letting go of the blade and trying to clench around it. He didn't know if Dean would follow through on the threat to leave it in all day, but he squeezed anyway.

"There's my sexy angel," Dean said, grinning as Cas distracted him by sucking on his fingers.

Cas closed his eyes, and as Sam watched, he nearly dropped the knife, because Cas was sucking on Dean's fingers like they were a cock, really putting on a show.

Dean used his free hand to open Cas' jeans, then he pushed them down, the material pooling around Cas' ankles along with the boxers. "You watchin', little brother?" he said as he pulled his fingers out of Cas' mouth and wrapped his arms around Cas and lifted, sitting his naked ass down on the table.

"Uhm, yeah," Sam said, trying to keep the knife in his ass without getting too distracted by what he was watching.

Dean took hold of Cas' plaid shirt and ripped it open, the buttons flying all over the room. Cas gasped, his eyes widening as Dean stepped over the material bunched around Cas' legs, stepping up to the edge of the table.

Sam squeezed his eyes shut for a moment, using the edge of the table to shove the knife back into him, hoping Dean wouldn't notice, and when he opened his eyes again, he nearly came right then and there, because Dean was fucking Cas hard and fast, arms wrapped around him as Cas held onto Dean's shirt, the material ripping a little, Cas' legs awkwardly flailing about, the jeans and boxers stuck on his boots.

Dean turned to look at Sam, smirking. "Forget somethin', Sammy?"

Sam groaned, backing up to the table and trying desperately to push the knife back in, but instead made it worse. It was terribly loud as it hit the floor, and Sam stood there staring at Dean, mouth hanging open.

"I'll deal with you when I'm done with fucking my angel," Dean said, then winked.

Cas whimpered and writhed as Dean pushed him back and spread him out on the table, fucking him hard, Cas' legs moving upward until Dean just grabbed them and put them over his shoulders, the jeans and boxers draped over Dean's back.

"You gonna come yet, Cas?" Dean asked, reaching out and stroking Cas as he fucked him.

"Mmmyeah!" Cas cried out, arms flung out on the table as if he was just there for Dean, ready to be used and put away wet.

Dean chuckled, and damn if it didn't make Sam's cock twitch. His ass felt open, empty, and a part of him didn't care that Dean was going to make him walk around with a knife butt plug because he knew it would give Dean more reasons to look, to touch, and to play with the both of them.

"Dean!" Cas said, back arching as his nails scratched at the surface of the table.

"C'mon," Dean said. "Wanna feel you clenchin' around me."

Sam looked up at Dean, having been focused on where he was slamming into Cas, and he'd completely missed the change in Dean. It had already happened somewhere along the line, but Dean was still fucking Cas hard, still teasing him with touches and that smirk on his face. But that was Dean stroking Cas' cock, and it was Dean that was waiting for Cas to finish before he came.

"Dean! Dean!" Cas cried out, coming all over his own stomach as Dean stroked him through it.

"Ah, fuck, Cas," Dean hissed, wincing as Cas clenched around him. He fucked into Cas again, once more, and then he was coming, leaning down, bending Cas nearly in half to kiss him.

Cas moaned into Dean's mouth, body rolling up against Dean as if he was still enjoying his orgasm, or maybe just happy to have Dean still inside him. Dean kissed over Cas' jaw, down his neck, and nibbled a bit on his shoulder before turning to look at Sam.

"What do we do with him, Cas?" Dean asked.

Cas turned, a lazy grin on his face, eyes half-lidded. "You already told 'im what you were gonna do to 'im," he said, words slurred.

Dean chuckled. "You're right. Okay, then let's head to the kitchen. I want a sandwich, and then I wanna watch some TV. Sam, you can go over my lap and I'll give you a break. I'll hold the knife so you don't have to."

Sam groaned, already sure that Dean was going to do more than just hold it. "Cas, help a guy out!" he said.

"You kiddin'?" Dean said as he stood up straight. "Cas is gonna be watchin' the whole time. And he's gonna be in charge of keeping his dick hard while he sits on the coffee table."

Cas frowned up at Dean. "Hey," he complained.

Dean pulled out of Cas and helped him up, Cas' legs a little wobbly. "Like the TV is gonna hold my interest. I need entertainment, gentlemen."

Sam rolled his eyes as he picked up the knife.

His asshole was sore by the end of the night, but Sam wasn't complaining. It was really fucking hot to be stretched across Dean's lap while Dean slowly fucked him with the handle, mostly ignoring Sam while Cas' cock became red and chafed from jacking it while sitting on the coffee table.

Dean didn't let them come until they were all in bed, wrapped around one another, and he'd fucked both of them. 

*

"Wait!" Cas cried out. "No!"

Sam was out of his room and sprinting down the hallway in nothing but his sleep pants before Cas' voice stopped echoing. While Dean could be fun with all the rough sex, there were times he was a little too rough. And those were the times it was a good thing they were a threesome as compared to just one of them with Dean.

Dean had Cas on the floor of his bedroom, Cas' sleep pants ripping as Dean yanked at them, and he was already trying to shove himself into Cas' hole. By the tone of Cas' voice, Dean hadn't prepared him at all, which was very unusual, even for this new Dean.

"Hey!" Sam said as he headed straight for a very naked and hard Dean.

"Back the fuck off!" Dean growled, not even glancing in Sam's direction.

But then Sam was on him, shoving him off Cas, and the two of them worked together. Dean was strong, but Cas and Sam were too.

"Get the fuck off me!" Dean yelled as Sam pushed him down onto his back and straddled his upper chest, his crotch in Dean's face, Dean's arms pinned to his sides.

Sam looked over his shoulder, smiling when he saw Cas straddling Dean's lower body, lubing himself up.

"I'm fuckin' horny," Dean said, not so much pissed at the turn of events as he was mad that he wasn't fucking somebody already. Dean liked sex, and he'd take it pretty much any way he could get it, but the aggression behind his actions sometimes was just too much now that he had the Mark of Cain.

Sam pulled his own cock through the slit in his sleep pants and smacked it down on Dean's lips. Dean scowled at him.

"Oh, you fucker!" Dean said, chuckling as Cas grunted, settling himself down on Dean's cock. "If you wanted to ride me, all ya had to do was ask."

Dean bucked, and Cas whimpered, grabbing onto Sam's shoulders for leverage.

"Not distracted enough?" Sam asked, smacking Dean's lips again.

"Nope," Dean said, smirking.

"Maybe you should open that pretty mouth," Sam said, purposely goading him.

Dean bared his teeth, clacking them twice. "Try it. I dare ya."

Dean normally didn't mind giving blowjobs. In fact he loved it. He was good at giving head and could get Cas and Sam off in record time with his skills, but when his eyes were dark, he was too aggressive, too unpredictable.

"Hand me the lube, Cas," Sam said. Cas gasped as Dean bucked again, but he handed Sam the lube.

"I hate the taste of that lube," Dean said, grimacing. "Put it in my mouth and I'll make sure you limp for the rest of the day."

Sam chuckled, then drizzled lube over Dean's neck.

"Dude!" Dean growled.

"Now you don't have to taste it," Sam said, giving dean his most innocent smile.

"Sam, don't," Dean said, voice low and threatening.

"Why?" Sam asked, as if he didn't know.

"You know why," Dean hissed. "Don't."

"I really have no idea what you're talking about," Sam said, then grabbed the base of his own cock and slapped it down on the left side of Dean's neck, the skin wet with lube.

"S-Sam, no," Dean said. "You do this, and I'll...," he said, trailing off as Sam smiled.

"What'll you do?" Sam asked.

"I'm gonna-ha!" Dean blurted, then looked up at Sam with side eyes, as if he couldn't believe Sam actually rubbed his cock over Dean's most ticklish area on his entire body. "Sam! Stop!"

"Why?" Sam asked, still feigning innocence.

Dean's eyes were locked with Sam's, and even though there were still black, Sam could tell his brother was emerging. "I'll put itching powder in every pair of your underwear for the rest of your life."

Sam shrugged. "I'll just start locking my underwear in a safe or something. It's worth it."

"No! Sam! Ha!" Dean said, breaking down into giggles as Sam fucked his neck, his cock sliding back and forth over Dean's sensitive skin. "S-Sam! Sam-hahaha! Sammy!"

Dean squeezed his eyes shut, laughing so hard that Sam couldn't help it and started laughing too. Soon Cas was leaning his forehead on Sam's back, laughing so hard he couldn't ride Dean anymore.

When Dean opened his eyes again, they were green. They could both feel the change even without seeing his eyes.

"You ready to stop being such an asshole?" Sam asked.

"Yes! Yes, just stop!" Dean yelled, losing his breath.

"All right," Sam said, starting to climb off Dean.

"No, wait," Dean said. "I won't bite. I'll get you off while Cas rides me."

"Yeah?" Sam asked, wanting to be sure. No leaving _that_ up to chance.

"Yeah, go ahead," Dean said, then opened his mouth.

"Oh, fuck yeah," Sam groaned as he pushed his cock into Dean's mouth.

Dean wasn't really in a good position to do much, but he still sucked and relaxed his throat as much as possible so Sam could push all the way in, then pull back out.

Sam groaned as Dean used the tip of his tongue to do some really fun things to the underside of his cock. Cas moved faster behind him, whimpering and gasping nearly constantly, his arms draped over Sam's shoulders, his breath hot on Sam's neck. Sam pushed all the way in and held himself there for a moment, letting Dean choke a bit and didn't pull out until Dean started to squirm on the floor.

That was it for Cas, and he was coming, hitting the small of Sam's back. After a final long moan, Cas collapsed against Sam's back.

"If you wanna come," Sam said, "you'd better get me off."

There was a challenge in Dean's eyes that had nothing to do with the Mark and everything to do with Dean being competitive. Soon Sam was coming down Dean's throat, not really paying attention as Cas climbed off and flopped down onto the floor next to them, panting and very satisfied. He always got overexcited when riding Dean.

Sam pulled out of Dean's mouth and scooted back, swiping his hand down his back, gathering some of Cas' release, and using it to open himself up, only pushing his sleep pants down enough to give Dean access to his hole. Dean watched him, eyes dark but still all Dean.

"Fuck yeah," Dean said as Sam lined up Dean's cock and lowered himself onto it. "That's so fuckin' hot."

Sam fucked himself so fast on Dean that he was bouncing, his hair flopping in his face, sweat dripping from the end of his nose onto Dean's chest. Dean lifted his hips, trying to fuck up into Sam as much as he could.

Suddenly Cas was grabbing Sam's face and kissing him, one hand on Dean's chest for leverage, the other in Sam's hair, holding him right where he wanted him.

"I like watching you ride him," Cas said against Sam's lips before biting and sucking and kissing him like he was trying to pull another orgasm out of Sam.

"Bite him, Cas," Dean said, smirking.

Sam gasped, his rhythm stuttering as Cas bit him hard enough that he knew he was bleeding a little. Dean used the distraction to turn them over, Sam flopping onto his back and blinking up at Dean for a moment before Cas shoved his tongue into Sam's mouth.

Dean set up a brutal pace, fucking him hard enough that Cas was having trouble keeping their lips locked, so he moved to Sam's neck and sucked, making Sam gasp.

"So fuckin' hot," Dean panted, then growled as he came inside Sam, finally dropping down onto Sam, sated and out of breath.

Cas pulled off of Sam with an obnoxiously loud slurp, leaving behind an impressive hickey.

"Dude, you're heavy," Sam complained.

"And sticky," Dean grumbled.

"Shower?" Cas asked.

"Too tired," Dean and Sam both said.

"Bed," Cas said, making the decision for all of them and grabbing Dean's arms, pulling him as he headed toward the bed.

The three of them climbed up on the bed and flopped down in a tangle of limbs, Sam's sleep pants caught just under the curve of his ass. They fell asleep wrapped around one another, the real Dean back with them until the next time.


	21. Sub Drop

**Summary for the Chapter:**

> **Anon Request:** Before I was here I was reading a subdrop fic (there are not enough!) and I was like, omg, I must request that if I can bc it would be awesome in your hands. So yeah, I would love if Dean was suffering from pretty severe subdrop and needed to be taken care of. I like Dean/Sam for this type of scenario. Any other kinks are fine!

**Notes for the Chapter:**

>  **Warnings:** Severe subdrop.
> 
>  **Tags for This Chapter:** Sam/Dean, Wincest, established relationship, off-screen BDSM, off-screen CBT, mention of oral sex and masturbation, sub drop, crying, caretaker!Sam, cuddling, aftercare

It doesn't happen very often, but when it does, Sam keeps his cool.

"Dean, tell me what five times two is," Sam says, his voice firm, though not loud. Not enough to startle, but enough to get Dean's attention.

"One, two, th-three, four five," Dean says, still covered in the load he's just blown, lying on his back, legs dangling off the end of the table and tied to the steel legs of the table, arms tied behind him, uncomfortable and putting a strain on his back, arms, and neck.

"Five times two," Sam says again, resting a hand on each of Dean's thighs, something to ground him if he's just a little out of it. "Tell me what five times two is, Dean."

"Two and five and two," Dean says, blinking up at the ceiling, covered in sweat, not shivering yet, but it'll happen soon.

"Tell me your name, Dean," Sam says as he unscrews the plates squishing Dean's balls, setting the contraption down on the table before gently pulling the plug out of Dean's ass. Next he tugs on the safety release binding Dean's legs to the table. It releases instantly and drops to the floor, a soft thump that makes Dean flinch.

"Sammy?" Dean says, voice cracking, breath becoming more shallow.

"Yeah, I'm here, Dean," Sam says. "Can you look at me? Look at me, Dean. Good boy," he says when Dean finally focuses on him.

"Sammy?" Dean says again, and this time his eyes well up with tears.

"C'mere," Sam says, sitting Dean up and letting him fall against the front of Sam's chest as Sam unbuckles the cuffs around Dean's wrists. "Can you tell me your name, Dean?"

"Dean," Dean says, then sniffles. "Sorry."

"It's okay," Sam says. "We were playing hard."

Sam rubs the feeling into Dean's wrists while Dean hiccups into Sam's chest, Sam's shirt getting wet with warm tears.

"Count to five for me," Sam says as he rubs Dean's forearms, Dean limp against him.

"One, two, th-I'm sorry, Sammy," Dean says, sniffling again.

"Keep counting," Sam says, moving up to rub Dean's upper arms. "You were doing good. What comes after two?"

"Three, four," Dean says, then pauses. "What d'you want me t'count to?"

"Five," Sam says, rubbing Dean's back, the skin already cooling and the sweat drying.

"Oh, okay," Dean says. "One, two, three, four, five."

"Good boy," Sam says, then picks Dean up, one arm under his knees, one behind his back, bridal style. Dean would kick his ass if he tried that move any other time, and even though Sam doesn't like why Dean's allowing it, he still enjoys holding his brother as he walks into the en suite bathroom and starts the water, setting Dean down on the edge of the tub.

"Cold!" Dean whines, clinging to Sam's left arm.

"I know," Sam says, keeping his voice soft. "We'll get warmed up together."

He doesn't wait for the tub to be full, and he doesn't bother stripping out of his clothes, just steps in and pulls Dean down between his legs, getting his ass onto the porcelain and leaning Dean's back against his own chest. He wraps his arms around Dean, resting his hands on Dean's belly and chest.

Dean immediately puts his own hands over Sam's and rests his head on Sam's shoulder. "I'm sorry," Dean says again.

"You were so good for me, Dean," Sam says, using Dean's name as much as possible and trying to distract him from the guilt that hits Dean hard whenever he has a bad case of subdrop.

"Sorry," Dean says, sniffling.

"You were beautiful," Sam whispers in Dean's right ear as he reaches for the plastic container he leaves by the tub for this very purpose. He snaps it open and grabs a small bar of chocolate. "You were a good boy. Did everything I told you to do."

Sam has already unwrapped the chocolate and left the little bars in a stack, so he just holds the bar up to Dean's lips.

"Open up," Sam says.

Dean doesn't have any inhibitions when he's like this. He doesn't question things or hesitate, and he trusts implicitly, so he opens his mouth and lets Sam put the little bar of chocolate on his tongue.

"Suck on it," Sam says, gently closing Dean's mouth and kissing the side of Dean's head.

"Sorry," Dean says around the chocolate.

"Is it good?" Sam asks. "It's some new stuff I got."

"S'good," Dean says.

Sam uses his toes to turn the faucet off, the water up to their chests and warm enough that Dean shouldn't have a problem with chills for a while.

"Thanks," Dean says.

Sam reaches into the plastic container and gets another piece of chocolate. Dean opens his mouth without needing to be told and sucks on the next piece.

"I'm sorry," Dean says.

"What was your favorite part, Dean?" Sam asks as he grabs a water bottle from inside the plastic container and opens it over Dean's belly.

"Huh?" Dean asks.

"Take a drink," Sam says, holding the bottle to Dean's lips. When Dean takes a few gulps, Sam takes the bottle away and sets it on the edge of the tub. "Good boy. Now think about what we just did, and tell me what your favorite part was."

"The chocolate," Dean says.

Sam chuckles, and Dean flinches, so Sam calms himself down. He knows Dean has no idea why Sam finds his answer funny. "Good chocolate, huh?"

"Yeah," Dean says. "Can I have more?"

"Yup," Sam says, grabbing another piece and putting it in Dean's mouth. "So how about when we were in the play room. What was your favorite part in the play room?"

"Oh," Dean says, elongating the vowel to the point where Sam has to bite his lip to keep from chuckling again. "The vibrator sleeve?" he says as if it's a question.

"You liked that?" Sam asks.

Dean nods. "Felt good. I came really hard."

"Take another drink," Sam says, holding the bottle up to Dean's lips. "Good boy," he says when Dean obeys him.

Sam runs the fingers of his left hand over Dean's chest, his right hand resting on Dean's tummy again.

Dean's breath hitches. "I'm sorry," he says.

"You didn't have a good time?" Sam asks.

Dean sniffles. "I did, but...," he starts, but then holds his breath.

"You wanna know what I liked best, Dean?" Sam Dean, trying to abort the anxiety attack Dean is working himself into.

Dean gasps, breathing again, distracted enough to forget about crying for the moment. "Yeah."

"Mmm," Sam moans as he kisses Dean's head. "My favorite part was when you realized the sleeve vibrated."

Dean lets out a noise that was probably a laugh, but he was too emotional, so it sounded like a honk.

"Your eyes got so big," Sam says. "You would've come right then and there if I hadn't stopped you."

"Bastard," Dean says, but he's smiling.

Sam smiled, happy to hear that Dean was feeling a little more like himself. "So what was the worst part?"

Dean's quiet for a moment, and just as Sam is about to say something, worrying Dean is getting stuck in a bad place, Dean speaks.

"When you blindfolded me and weren't touching me," Dean says softly.

"Yeah, I know you have a hard time with that," Sam says, kissing the side of Dean's head and giving him a squeeze with his arms. "But you're just so good for me. I love watching you do stuff you're not all that thrilled about because you try so hard for me, and when you do it, I get to reward you."

Dean chuckles. "You _did_ reward me. You sure got a purty mouth, boy."

Sam snorts. "Yeah, I need to remember to gag you when I suck your cock. I really didn't need that image in my head."

"Big baby," Dean says, jabbing Sam in the ribs with his elbow. "Gimme more chocolate."

Sam sighs dramatically, as if Dean's horribly demanding and it's hard to put up with him as he grabs another piece of chocolate and hand-feeds Dean.

"Hey, did you come?" Dean asks.

Sam lets out a chuckle. "You didn't notice? That wasn't just your jizz on your stomach."

Dean hums contentedly. "Yeah, I was hot. You couldn't help yourself."

"Yes, Dean," Sam says, rolling his eyes, "you were devastatingly sexy and I blew my load without even stroking my dick more than twice."

"Really?" Dean asks, craning his neck to look sideways at Sam.

"You'll never know," Sam says. "You weren't paying attention."

Dean turns around, straddling Sam's thighs and resting his forearms on Sam's shoulders. "You'll tell me."

Sam smirks. "I will?"

Dean nods. "Yup. I won't even have to try that hard to get the truth outta you."

"Huh, you sound a little too confident," Sam says, wrapping his hands around the curve of Dean's ass cheeks.

"Oh, I am," Dean says.

"Okay, go for it," Sam says. "Lemme see your-ow!" he yelps, his back arching as Dean twists his nipples. "Okay! Okay! You were so fucking hot I blew my load after barely even touching my cock!"

Dean lets go and grins at Sam, unrepentant. "I won," he says, then blows a raspberry on Sam's neck and climbs out of the tub.

"Dude!" Sam says, feigning hurt. "I was all comfy and snuggling with you!"

"You'll get over it," Dean says, reach out, offering a hand to Sam. "I'm tired. I'll let you snuggle with me in bed as long as you let me sleep."

Sam takes his hand and stands up in the tub. "Lemme get outta these wet clothes," he says.

"Sammy, Sammy," Dean says, shaking his head. "I thought I raised you right. You're supposed to take your clothes off _before_ you get in the tub."

Sam glares at him. "Really?"

"Yup," Dean says, then grabs a towel from the stack on the shelf and wraps it around his hips. "Don't forget to clean up after yourself."

Sam huffs as Dean walks out of the bathroom and leaves him to clean up the mess. He shakes his head, smiling as he unplugs the tub and wipes everything down. Dean's half asleep by the time he crawls into bed with him, but Dean still lets him cuddle.


	22. Swings Both Ways

**Summary for the Chapter:**

> **Anon Request:** For the ask box thing, since you write so wonderfully ❤️ could you do one where Dean comes out to Sam as bisexual, and he's afraid of what Sam might think, but Sam is okay with it. But later on Sam sees a group of men harassing dean about it, touching him and yelling at him, and Sam's anger explodes!! Super-protective Sammy please?

**Notes for the Chapter:**

>  **Warnings:** Homophobic slurs/ **homophobic language** , homophobia, violence against homosexuals (Dean).
> 
>  **Tags for This Chapter:** No on-screen pairings, but implied Dean/OMC and Dean/OFC, homophobic slurs, protective!Sam

Just like everything else Dean does, he jumps in head first, yet he still does it strategically. And Sam wouldn't have it any other way.

"The door swings both ways," Dean says, smirking at Sam as he holds the door for him, "just like me!"

It's flippant and said as a joke, but Sam knows better. The lingering looks at women _and_ men, the nights when Dean doesn't specifically say "she" when he talks about who he slept with, and some of the other jokes over the years finally make sense. Sam wishes he was more observant, but sometimes he's just not.

Sam snorts. "Dork," he says, shaking his head as he walks into the restaurant and makes his way to the counter.

Dean has a funny look on his face, a bit of fear in his eyes as they get their food and sit down, but Sam knows his brother all too well.

"So if you _had_ to choose," Sam says, and he sees Dean tense, hold his breath, waiting for Sam to say something he can never take back, "Angelina or Brad?"

Dean blinks at him for a moment, mouth dropping open just a bit, the wheels in his head turning. And then he grins. "It's cruel to make me choose, but damn, I think I'd have to say Angelina," he answers, chuckling.

Sam laughs. And that's it. Dean came out of the closet he'd spent thirty-two years hiding in, Sam still loves and accepts him, and a weight has obviously been lifted from Dean's shoulders. Sam doesn't know what prompted Dean to come out now instead of years ago, but it's okay. Sam knows it's hard, facing possible rejection even though he's never said anything homophobic in his life that would make Dean think Sam would hurt him like that.

Nothing changes between them. Dean still flicks his straw at Sam, spraying soda on his face, and Sam still tries to trip him as they're leaving.

*

Sam doesn't think much about it. He really doesn't care. And Dean gets bolder around him, mentioning how hot a male suspect's ass is after they leave the man's house, cracking a joke about how he'd be totally up for a threesome with the married couple who owns the bar they have dinner at, and even using a male pronoun when describing some of his one-night stands.

But it's not something that's on Sam's mind all the time. Dean's still Dean, no matter who he chooses to fuck. So when Sam comes back from the bathroom to find Dean surrounded by seven guys, he just assumes Dean has been hustling pool.

"Fuckin' faggot," Homophobic Asshole #1 says, poking Dean in the chest.

Sam's not scared. The guys aren't small, but they're also not the picture of health, if their beer bellies are anything to go by, and Dean doesn't look worried yet.

"You wanna suck some dick?" Homophobic Asshole #2 says, sneering at Dean from behind as he bumps his chest into Dean's back.

Dean sighs. "All right, fellas, I think you've had a little too much to drink. None of you are my type, so let's just call it a night."

"He asked you a question, fuckboy," Homophobic Asshole #3 says. "We're not faggots like you, but a mouth is a mouth, and since you're such a slut for it, we'd be willin' to let you suck us all off."

"That's very nice of you to offer," Dean says, "but-hey!"

Something inside Sam snaps when Homophobic Asshole #4 grabs Dean's crotch and won't let go. Dean can fight. Sam knows this. But they crossed a line with the slurs, and the crotch grabbing went way over the limit.

A kidney punch to Homophobic Asshole #5 followed by a kick to the back of Homophobic Asshole #6's knee takes them both down to the floor. #1, #2, and #3 all turn to stare at Sam like he's a ghost while #4 and #7 decide to take on two hunters who have been trained to fight since they were kids.

Sam takes a glancing blow to his left side from #7, but quickly knees the guy in the balls and shoves him into the pool table, the man's head making contact with the wood and most likely leaving a nice lump, though no serious damage. The guy crumples to the floor, holding his head and whimpering.

Homophobic Asshole #1, #2, and #3 have recovered, and while Dean takes #4 out with a punch to his neck, Sam growls as #3 sucker punches Dean in the side of the head. Dean goes down to his knees, but #3 never has a chance to do any more damage as Sam tackles him and sends him crashing through the back window.

Sam turns to Homophobic Asshole #1 and #2, smirking as they try to decide whether they should run or fight. Sam makes the decision for them, grabbing the pool cue and cracking it over the back of #1 as he tries to run, then jabs the remaining part into the stomach of #2. It doesn't break the skin, but it'll leave a colorful and painful bruise. Homophobic Asshole #2 tries to catch his breath while crawling away, and Sam adds insult to injury by kicking his right ass cheek, sending him sprawling.

Dean punches Homophobic Asshole #5, who squeals as he runs away, and Sam simply scowls at Homophobic Asshole #6, who has recovered from the blow to his knee enough to limp away.

"I could'a taken 'em," Dean grumbles, but Sam hears the pride in Dean's voice.

Sam smirks. "I didn't wanna let you have all the fun."

"I feel like pizza," Dean says, slapping Sam's right arm. "Do you want pizza?"

"Yeah, I could eat," Sam says, nodding.

"Let's get outta here," Dean says, brushing by Sam and heading for the door.

Sam chuckles as he follows Dean out of the bar, leaving several bleeding, whimpering men behind.


	23. Five Times Sam Was Topped 2

**Summary for the Chapter:**

> [Sandra's](https://archiveofourown.org/works/4463927/comments/38119871) request for my [Tumblr Ask Box Requests](http://mayalaen.tumblr.com/post/122749813129/ask-box-requests) ([on AO3](http://archiveofourown.org/works/4244124/chapters/9603369)). Sandra's Request: Wonderful fic, I love when big man like Sam bottoming, this is so hot, I'd like see him fucked by Dean and Charlie any chance for sequel?”
> 
> The first chapter of this fic was originally a sort-of request by [samanddeaninpanties](http://samanddeaninpanties.tumblr.com/). These vaguely follow canon, but not really, just like the first chapter.

**Notes for the Chapter:**

>  **Please Note:** If you’d like to avoid the Wincest, just skip parts 3 and 5, which are labeled as Sam/Lisa (with voyeur!Dean) and Sam/Dean. The rest of them don’t mention Sam/Dean other than Dean wanting to know what’s going on and Charlie talking about teasing Dean with details, which can totally be taken as horny!Dean wanting details about Charlie’s sex life, not necessarily about Sam.
> 
>  **Tags for This Chapter:** Sam/Jess, Sam/Pamela, Sam/Lisa with voyeur!Dean, Sam/Charlie, and Sam/Dean, pegging, manhandling, rough sex, biting, light spanking, strap-ons, dirty talk, light D/s, tickling, begging

I'm posting a notice here, but please go to [Chapter 2 of Five Times Sam Was Topped](http://archiveofourown.org/works/4463927/chapters/11957924) to read this fill. It works as a standalone or as a second chapter to that fic. Even though the request was from my [Tumblr Ask Box Requests](http://mayalaen.tumblr.com/post/122749813129/ask-box-requests), I'm adding it to my fic because it fits well and I like the flow.

Enjoy :)


	24. Prosodic Stress

**Summary for the Chapter:**

> This is soupernabturel and assbuttintheimpalafiction‘s fault: [This Post](http://assbuttintheimpalafiction.tumblr.com/post/134153078728/soupernabturel-just-shower-thoughts-the) from Shower Thoughts read “The sentence “I never said he licked my asshole” has 7 different meanings depending on the stressed word.” So of course soupernabturel had to say “I need a Destiel fic showing all the different ways you can use this sentence, don’t ask me why I just do” and assbuttintheimpalafiction followed that up with #yessssss · I'll settle for any that have bottom!cas.
> 
> I went with different pairings because I thought it might get boring with just Destiel, but the first and last ones are Destiel. For an explanation of prosodic stress, [Click Here](https://en.wikipedia.org/wiki/Stress_%28linguistics%29#Prosodic_stress). Or just read the fic and you’ll understand :D
> 
> Even though this wasn't one of the fics someone asked me for, I'm posting it in the Tumblr Ask Box Requests because it's short, someone mentioned it on Tumblr, and I want to, so :P

**Notes for the Chapter:**

> **Pairings and Warnings/Tags for Each Part**
> 
>   1. Dean/Castiel, oversharing, humiliated!Sam.
>   2. Meg/Castiel, D/s, roughness, manhandling.
>   3. Sam/Dean/Castiel, Wincestiel, D/s, talk of punishment/spanking.
>   4. Bobby/Crowley, Crobby, humiliated!Dean, humiliated!Sam, mention of Sam/Crowley.
>   5. Sam/Gabriel, Sabriel, humiliated!Dean, sort of sex in public.
>   6. Dean/Benny, Denny, humiliated!Sam, mention of Benny/Cas.
>   7. Dean/Castiel, Destiel, humiliated!Dean.
> 


**1\. The Destiel Version**

" _I_ never said he licked my asshole."

Sam cringed. "Can't this wait until later? And, ya know, when we're not in public?"

"Well I didn't!" Dean insisted. "Cas is the one that opened his big mouth and told you about what goes on in the bedroom this time, not me."

"Dean, just drop it," Sam said, taking a quick look around to see if anyone was listening in on their conversation in the middle of Walmart.

"You're always complaining that I give too many details about our sex life," Dean said as he tossed a loaf of bread into the shopping cart. "But _I_ didn't go into detail about the ass licking thing. He did. So quit giving me a hard time about it. I can't stop him from oversharing."

"Okay, okay, just shut up!" Sam said, waving his hands in Dean's face. "I'll never give you a hard time ever again. Just shut up!"

Dean smirked as Sam stomped into the next aisle.

**2\. The Megstiel Version**

"I _never_ said he licked my asshole."

Meg grabbed a handful of Cas' hair and yanked him closer. "He better not have touched you. You're mine. If your asshole gets licked, it's going to be my tongue."

Cas gasped as she pushed him against the wall. "Please. I want to know what it feels like. Please!"

Meg chuckled. "I'll take care of you. Don't worry. When I'm done with you, you won't even remember your own name."

**3\. The Wincestiel Version**

"I never _said_ he licked my asshole."

Sam pinned him with a look that spoke volumes. "You may not have said it, Dean, but do you really think I have no idea what noises you make when someone's licking your asshole?"

"Okay, but-"

"You were grounded," Sam said. "What does that mean, exactly?"

"It means," Cas said from the corner of the motel room, "that we're not allowed to have sexual intercourse."

"No," Sam said, frowning at Cas' back. "And keep your mouth shut when you've got your nose in the corner."

"It means that we can't play," Dean grumbled. "But we were really horny!"

"You're still getting spanked," Sam said. "Both of you."

"Aww, man!" Dean whined.

**4\. The Crobby Version**

"I never said _he_ licked my asshole."

Bobby glared at Crowley, ready to jump over the desk and punch that smug look right off the demon's face.

"Well, this was much more information than we really needed," Dean said as he backed out of the room, hands up.

"You sure?" Crowley asked, raising his voice so Dean could hear him even though he was practically running out the front door. "Because I don't mind sharing."

"Shut up," Bobby said, standing up.

"What are you getting so worked up for, sweetheart?" Crowley asked. "Are you jealous I let Sam lick my asshole? Because it's all yours now. I wouldn't dream of letting Sam lick it now."

Sam tried to will the floor to open up and swallow him, but it didn't.

**5\. The Sabriel Version**

"I never said he _licked_ my asshole."

Dean blinked at Sam. "Excuse me?"

Sam squirmed on his seat in the restaurant. "I said," he hissed, leaning closer to Dean, "that he never _licked_ it."

"So he, what, gave you an angel STD?" Dean asked.

Sam rolled his eyes. "No." He squirmed, wincing as he nervously moved the silverware around on the table.

"Then why can't you sit still?" Dean asked, pushing his plate aside.

"Because Gabriel's doing something to me," Sam hissed. "But it sure as hell isn't licking!"

Dean's eyes widened as he realized Sam's response was present tense, not past tense. "Like right now?"

"Oh, oh, fuck," Sam whispered, hands balled into fists as he hunched over. "Oh, fuck, G-oh! Oh, fuck. I-oh. G-Gabe, you fucker. Oh, fuck," he whimpered, then dropped forward, his forehead hitting the table as his body shook with spasms.

"Would you just fuckin' apologize for calling him short already?!" Dean growled as he stood up and walked out of the restaurant, leaving Sam in the booth, wet spot on the front of his jeans growing bigger.

**6\. The Denny Version**

"I never said he licked _my_ asshole."

"I didn't ask!" Sam yelled. "Stop talking! Ugh, I didn't even fucking ask!"

Dean smirked as Sam stormed out of the motel room. He turned to Benny. "Well, you never did lick _my_ asshole."

"Hmm, we should probably fix that," Benny said. "Wouldn't want ya gettin' jealous'a Cas."

Dean grinned, already unzipping his jeans.

**7\. The Destiel Version, Again**

"I never said he licked my _asshole_."

Dean's face flushed. And really, he shouldn't have to put up with shit like this. Except he did have to. Because Cas had no boundaries, no shame, and apparently Mrs. Schaeffer had no boundaries either.

Mrs. Shaeffer grinned. "Oh? Well, maybe you should try it. It's very fun, dear."

Dean felt the tips of his ears heat up. "We need to leave now, ma'am. I'm sorry to have bothered you."

He grabbed Cas' arm and dragged his stupid angel boyfriend out of the sex shop. It was obvious she wasn't a witch, just a very knowledgeable and helpful sex shop owner who could tell without even asking that Cas needed to open up more and ask for things in their relationship. The FBI badges hadn't fooled her for a second.

"Your face is red," Cas commented as they got into the car.

"If you never mention this again," Dean said, staring straight forward out the windshield as he turned the car on, "I promise I'll lick your asshole so good tonight that you'll come without ever touching your dick."

"What sex shop?" Cas asked.

It was said with so much innocence that Dean did a double take. Good. Cas got it. And he was going to get it later tonight.


	25. Caught You

**Summary for the Chapter:**

> Radioactivegleek's Request: I'm going to request a fic here since I don't have a tumblr. Can you do a fic where Sam catches Dean using a pacifier, and decides that he'll treat Dean like a baby since he's acting like one? That would be great, thank you.

**Notes for the Chapter:**

>  **Warnings:** Mildly dub-con non-sexual infantilism.
> 
>  **Tags for This Chapter:** Non-sexual infantilism, diapers, bottles, pacifiers, witches, temporary impairment from witch's powder, mildly dub-con in that Dean fights it a little and Sam takes advantage of Dean being a little out of it.

Sam sneaks into the motel room several hours after he and Dean split up. He's quiet, doesn't want to wake Dean up even though he knows he probably will. Dean had been exhausted from the hunt, and it had been a rough one. Kids always made hunts hard for Dean.

They'd split up at the bar, and Sam had been flirting with a very beautiful woman, so Dean waved him off, said he'd be heading to bed, and that he wouldn't wait up for him.

Sam could hear the soft snores, but the light on the nightstand was still on. Dean must've fallen asleep as soon as his head hit the pillow, because he was still in his jeans, boots, and shirts, curled up with his back toward the door. Sam locked the door, then set his wallet on the dresser.

"Oh, fuck," Sam breathed, doing a double take and finally flat out staring at his brother. He felt like rubbing his eyes, because he couldn't have been seeing what he was seeing.

Sam took a few steps closer to Dean's bed, peering down at him, mesmerized by the movement of the pacifier in Dean's mouth. Dean was sucking on it, even in his sleep.

Dean shifted, then his eyes opened. When he caught sight of Sam, he flinched, not having expected Sam standing there, but then he must've realized why Sam was staring. In a flurry of movement, Dean sat up, knocking the pacifier out of his mouth and shoving it under his pillow.

"So," Sam drawled, prodding Dean a little.

Dean looked like a deer caught in the headlights. His mouth was slightly open, his lips wet with spit and plump from sucking on the pacifier, eyes wide, and a soft blush on his cheeks.

And then Dean's walls came up, his eyes hardened, his lips thinned into a tight line. "If you ever speak of this again, I'll kick your ass," he said, voice gruff, then flipped over and settled down with his back to Sam.

Sam undressed, a smirk on his face. And it was still there when he climbed into bed and turned the light off.

*

Dean was really fucking out of it. He was drooling and his eyes were half-lidded, mouth not working right even when he did try to say something.

"Hang on, Dean," Sam said, patting his brother's stomach as he pulled into the driveway of their motel.

"Is'a wee, S'my," Dean said, falling over onto Sam's right shoulder.

"Yeah, I know it was a witch," Sam said, turning the car off. He slid out, taking Dean with him, then hefted him onto his shoulder and took him into their room, thankful the neighborhood was shitty so nobody noticed or cared about what he was doing.

"Huh mah ton," Dean said, poking at Sam's back as Sam locked the door.

"Yeah, you bit your tongue when you fell," Sam said as he set Dean down on the bed. "That's why it hurts."

He started undressing Dean, and that's when everything changed. Just as Sam pulled Dean's jeans down, lifting Dean's ass off the bed just enough to get them over his ass, Dean let loose.

Sam sighed as the strong scent of urine filled his nose. It wasn't a lot. Dean's bladder hadn't been full, but it still soaked Dean's boxer briefs and the lower part of his shirt.

"Dean, I'll be right back," Sam said, patting Dean's belly. "Don't move. I'll be right back."

"K'S'my," Dean said, eyes closing.

Sam went out to the car and grabbed his duffel bag, then headed back into the motel room, where Dean was snoring. Sam set the bag on the bed and pulled out the wipes, a diaper, and the powder.

It wasn't hard to get Dean out of his clothes. He was dead weight, but it wasn't the first or even hundredth time he'd dealt with an injured or unconscious Dean. Once he had Dean naked, he wiped him clean with the baby wipes, slid a diaper under his ass, powdered Dean's crotch, then fastened the tape. He searched Dean's duffel for a pair of sweats and a clean T-shirt, then put those on Dean as well.

Soon Dean was curled up under the blanket, pacifier in his mouth and blissfully sleeping off whatever Dean had dumped on himself. Sam knew it wasn't dangerous. The witch was long gone, but she'd left her formulas behind, and the powder combination Dean had created by knocking the cupboard off the wall was enough to relax, but not so much as to kill.

Dean would be okay. And Sam felt relieved once he'd made his decision.

*

Dean slept through the night and even through Sam picking him up and setting him on his lap, but he started to stir when Sam checked his diaper.

"Wha's. What's goin' on?" Dean asked, eyes opening wide and the pacifier falling out of his mouth.

"Are you hungry, little one?" Sam asked, reaching for the bottle and holding it to Dean's lips.

Dean blinked at him for a moment, then pushed back. Sam caught him before he fell on his ass, but by then Dean realized he had a diaper on and started pulling at it.

"That's enough, Dean," Sam said, giving Dean's bottom a thump.

"What the fuck are you doing?" Dean asked, twisting and trying to get away.

"Just calm down," Sam said, holding on and waiting Dean out.

"Let me go!" Dean yelled.

"It's okay, Dean," Sam said, holding Dean close and patting his back, rocking them back and forth. "Everything's okay, little one."

Dean's body remained stiff, but at least Dean shut his mouth. Sam held the bottle up to his lips again, but Dean turned his head.

"I think you'll like it," Sam said. "This one's apple pie flavored."

Dean glared at him, but then glanced at the bottle. Sam saw as realization hit Dean, and he cheered internally, because Dean's body was relaxing.

"There you go," Sam said, his hold on Dean becoming more gentle as he encouraged Dean to lie back. He held the bottle to Dean's lips and waited.

Dean looked him in the eye, desperately searching for any hint this was a big joke, that he was going to be ridiculed and made to feel like a disgusting pervert, but Sam just waited him out.

"After you finish your bottle, I'll give you a bath and a fresh diaper," Sam said, running the nipple over Dean's bottom lip. "I've got some bath toys for you to play with. Does that sound like fun?"

Dean slowly opened his lips, and when Sam pushed the nipple into his mouth, Dean started sucking.

"There's my good boy," Sam said, smiling, and he didn't miss the fact that Dean relaxed even more against him. Maybe later I'll read you a story from the new books I got for us. Would you like that, Dean?"

Dean groaned as he finally had relaxed enough to taste the milk coming out of the bottle. He nodded, sucking harder.

"Okay, we'll do that later," Sam said. "And if you're a really good boy, I'll rock you to sleep tonight. Just you and me. My good little boy."

Dean gazed up at him, and everything Dean would never say came through crystal clear to Sam. Dean would have never asked for this. Would never have even mentioned it. But now he had it, and there was a contentment in his eyes that Sam felt, almost like something tangible.

Sam knew it wasn't going to be easy. Dean would fight it at times. But if this is what Dean wanted or needed, he'd get it.

"Is that a good bottle, Dean?" Sam asked.

Dean nodded, sucking harder and closing his eyes.


	26. Save Room for Pie

**Summary for the Chapter:**

> Anon Request: For your tumblr ask box request i would love you forever if you wrote some chubby!Dean/Sam where Dean is more than a little chubby. Dean can either be really self conscious or just totally proud and unashamed. I'm picturing Dean gained all the weight while Sam was in Hell and so it's a surprise when Sam finds his way back to Dean! It's a little weird for Sam but he loves Dean any way he can get him.

**Notes for the Chapter:**

>  **Warnings:** None.
> 
>  **Tags for This Chapter:** Sam/Dean, chubby!Dean, food play, blowjob
> 
>  **A/N:** Chubby/fat play isn’t one of my kinks, so I hope I did this justice. I’m ignoring the whole robo!Sam thing even though I really, really like robo!Sam because it just doesn’t work with the timeline.

Sam still can't get over it. He's been back on the road with Dean for a few months and yet it's not the Dean he left in Stull Cemetary.

"Oh, man, I'm stuffed," Dean says as he shoves the empty containers away and gets up from the motel room table. "You get any dessert?" he asks as he looks to Sam, hope in his eyes.

Sam chuckles. "Yeah, of course I did."

Dean smiles. "Yes!" he says as he heads for the bed he's claimed as his for the night and flops down on it, the bed groaning a little more than it would've just a year ago. "Serve me, bitch!"

Sam rolls his eyes, but he doesn't hesitate to grab the bag of single-serve pies and walk over to the bed. He climbs on and dumps out the contents of the bag.

"I can't eat all that," Dean says, pointing at the pile.

"It's not all for you," Sam says as he opens one of the packages and scoops out a finger full of banana cream pie. He holds his finger out to Dean, but just as Dean tries to lick it clean, Sam pulls it away and shoves it in his own mouth.

Dean pouts, the chubbier cheeks making him look even more adorable. "Dude!"

"Yeah, Dean?" Sam says, all innocence.

"Pie!" he says as he snatches the little container from Sam's hand.

"Hey!" Sam says, trying to act affronted, but instead he just laughs when Dean pokes his finger into the pie.

Sam stops laughing immediately when Dean pulls his shirt up and smears the pie on his nipple.

"You want some?" Dean asks, smirking.

Sam puts his hands on Dean's belly, loving the way it's more substantial, fuller. Dean pulls his shirt off over his head and tosses it in the corner of the room. Sam slides his hands over the love handles, up Dean's sides, and leans down to lick at the pie. Dean moans, and Sam hears him gasp as he sucks on Dean's nipple.

Dean grabs another container and rips it open while Sam reaches down and opens Dean's jeans up. The jeans are a few sizes bigger than what Dean used to wear, and Sam groans when he finds lacy material encasing Dean's cock and balls.

Sam looks down and smiles. "You're wearing them," he says.

Dean chuckles. "Well yeah. They feel great."

Sam's chest feels tight, because he'd bought them for Dean. He'd walked into the plus size lingerie store and picked them out just for Dean. They're pretty and lacy and pink, and there's a cute little pink bow on them.

"So fucking hot, Dean," Sam says.

Instead of blushing, Dean spreads his legs for Sam, lifting his hips off the bed, trying to get Sam to do something, to get more friction where he needs it. This is what Sam loves. The same guy who was shy when he was younger, always worried about what people thought of him, always hiding under layers of clothes. The same guy who blushed the first time Sam said he was beautiful. The same guy who shamelessly did a striptease for Sam the first night they were back together. The same guy who's finally comfortable in his skin and confident with his body.

Dean's got his finger in the pie, grinning at Sam, and Sam nearly comes in his jeans when Dean reaches down and pulls his cock out of his pretty little panties, then smears the pie over the head of his cock.

"You want some?" Dean repeats, waving his cock at Sam.

Sam doesn't hesitate to suck him down, holding onto Dean's big ass with both hands, and when Dean comes, yelling Sam's name and yanking on his hair, Sam takes it all before shoving Dean over and onto his belly, pulling his jeans and panties down, and rimming Dean until his brother comes again, moaning and writhing beneath him.

It still surprises Sam. Dean doesn't turn as many heads as he used to, doesn't get called pretty boy by leering truck drivers, but Sam thinks he's gorgeous, and seeing Dean happy and content is all Sam ever wanted anyway. Wrapping his arms around Dean's belly while he fucks him from behind, unable to do more than just barely get the tips of his fingers to touch because Dean is so big, well, that's just icing on the cake, because now there's more of Dean to love.


	27. A Good Bitch

**Summary for the Chapter:**

> **[Anon's Request:](http://mayalaen.tumblr.com/post/129447335829/hi-maya-i-have-a-request-just-watched-dog-dean)** Hi maya, I have a request. just watched dog Dean episode again, wanted dogdean and his caretaker sam? The spell Dean put himself never wears off. So he behaves more like a dog and Sam should watch over him not to sniffing around:) Dean rather whining or barking than talking. Sam should help him wearing clothes, bathing, lacing up his boots, using tools. He even goes to rut, humping over sam's thigh when theyre sleeping, Sam fucks him like a bitch.(bottomdean please!):D Thanks for awesome works!

**Notes for the Chapter:**

>  **Warnings:** None.
> 
>  **Tags for This Chapter:** Sam/Dean, puppyplay (kind of), spells/curses, dog!Dean, fucking/anal sex, mild dirty talk

Dean whines, sitting by his bowl. When Sam doesn't notice, he whines again and nudges the bowl with his nose. Sam is still typing away on his laptop, so Dean barks.

"Dude, I'm almost done," Sam says, not even looking Dean's way. "I'll get us some food in a few minutes."

But Dean's hungry, so he crawls over to Sam and growls, taking the cuff of Sam's jeans between his teeth and tugging.

Sam chuckles, closing the laptop. "All right, all right. I'll get dinner."

Dean yips happily, wagging his tail. Or actually wriggling his hips because he doesn't have a tail, but Dean forgets nowadays.

"Be a good boy," Sam says, grabbing the keys. "I'll be right back. No barking."

Dean pants as he sits on the floor in the middle of the motel room. He waits there the whole time Sam's gone, and when he hears the door open, he starts wagging his tail again, excited that dinner and Sammy are home.

*

They didn't know it at the time, but the spell becomes permanent if left too long. There's no specific time period, but rather it's all about how deeply rooted the spell gets, and it sank right down into Dean like it was meant to be.

Dean pants and slobbers on Sam's neck as he humps Sam's leg. Sam groans, trying to shove Dean off. But Dean just keeps it up.

"I'm almost done," Sam says.

Dean nips Sam's neck.

"Hey!" Sam yells, but then sighs when Dean pouts at him. "Okay, I've been ignoring you since dinner. I'm sorry."

Dean wags his tail, hopeful, and when Sam grabs the lube off the table, slicks his fingers up, and pushes them into Dean, Dean happily yips and slobbers all over Sam's face.

Sam chuckles. "Okay, okay. Down. Get down."

Dean does as he's told, then turns around on his hands and knees, presenting his ass to Sam, wagging his tail.

"Good girl," Sam says, slicking up his cock and getting down onto the floor behind Dean. "Such a good bitch."

Dean whines, spreading his legs wider for Sam as Sam lines up his cock and slides in. Sam fucks him hard, like the bitch in heat he is, not bothering to touch Dean's cock because Dean's such a slut for it that he comes with just a cock in his ass.

"So fuckin' tight," Sam hisses.

He almost knocks Dean over as he fucks him hard, coming inside Dean even as Dean's asshole clenches around him, Dean yipping with excitement as he comes all over the carpet.

Sam pulls out and pets Dean's back. "Clean up your mess," he says as he gets back onto the chair and continues his research.

Dean calmly laps at the floor, content and sated now that he's been fucked. When he's done cleaning his mess, he sits next to Sam, smiling when Sam reaches down and gently scratches at his scalp, calling him a good dog.


	28. Show Me

**Summary for the Chapter:**

> [**jsquaredfever's Request:**](http://mayalaen.tumblr.com/post/132075936769/im-currently-reading-your-tumblr-ask-box-requests) Im currently reading your Tumblr Ask Box Requests on AO3 and have a request for you. Could you do a Sam Winchesterl/Castiel explicit story involving oral sex hard anal sex and lots of water sports please? Thankyou x Yeah, top Sam/ bottom Casiel please x

**Notes for the Chapter:**

>  **Warnings:** None.
> 
>  **Tags for This Chapter:** Sam/Castiel, rough sex, fucking/anal sex, piss play, piss drinking, manhandling, handjod, mild D/s

Sam fucks him harder, grabbing a handful of Cas' hair and yanking, Cas' back bowing as Sam fucks him over the table in the library. Cas' slacks and boxers are down around his ankles, his tie almost falling off, and his coat is bunched up around his underarms.

"Sam, Sam, Sam," Cas chants, a whisper, like he doesn't even realize he's saying it over and over, breathy little voice from a creature that could eviscerate Sam without breaking a sweat.

Sam pulls out and steps back, watching as Cas falls to the floor, then scrambles to his knees and waits, mouth open. An angel is on his knees, begging Sam to use him, and Sam can't imagine anything else ever topping this.

"You want this?" Sam asks, waving his cock back and forth.

"Please!" Cas says, knee-walking closer.

Sam smiles, because Cas really does look adorable on his knees, hair sticking out all over because Sam can't keep his hands out of it, eyes wide and blown from arousal, and mouth open and waiting. Cas closes his eyes when the first splashes of piss hit his chin, then Sam get it in his mouth. Just enough to get him wet.

"C'mere," Sam says, cupping the back of Cas' head and pulling him onto his cock.

Cas chokes, and it turns Sam on even more, because he knows Cas has complete control over his vessel, and there's no real reason Cas should gag other than he knows Sam likes it.

"Oh, fuck," Sam hisses as Cas moans around his cock, and that's it, Sam's done. He's coming down Cas' throat and holding Cas close, his nose in Sam's pubic hair.

It takes him a moment to relax enough, but when he does he lets loose with the rest of his bladder, watching as Cas' eyes open wide, chuckling as Cas gags again, but manages to swallow it all.

When Sam's done, he pulls out and slaps Cas' face with his cock, a wet thwack that makes Cas moan. Sam doesn't bother putting himself away, and instead he bends over and grabs Cas, hefting him onto the library table, bare ass on the wood, and jerks Cas off fast and rough, just the way he likes it.

Cas cries out, falling against Sam, his hands clawing at Sam's arms. Finally Cas settles and just pants against Sam's shirt.

"Better?" Sam asks.

Cas looks up at him and grins. Fucking grins! "No. I think you should show me who I belong to again."

Sam shakes his head, chuckling. "I didn't say I was done with you."

Cas yanks him close, fingers tight in his shirt, and kisses him, face still wet and messy. When he finally pushes Sam away, he's smiling. "Good."


	29. Holding On

**Summary for the Chapter:**

> This is my first reader insert fic. I was asked by an anon to write a Boyking!Sam x Reader fic and this is what my brain decided to write, but since I have no clue who the anon is and they never asked for Wincestiel, I wrote a second one (which will be in the next chapter), but that means this one is inspired by that request and not really a fill for it.

**Notes for the Chapter:**

>  **Warnings:** Dark/Boyking!Sam fic set in Hell
> 
>  **Tags for This Chapter:** Boyking!Sam/Dean/Reader(Cas), reader insert, set in Hell, discussion of off-screen torture  & awful shit, mention of off-screen Wincestiel sex and relationship, depression, injury

It feels like you've been here forever. Scared. Alone. Cold. You knew Hell was cold. You'd been there before to save Dean. But you didn't know back then how it would seep into your entire being, chipping away at what's left of your grace. You were a warrior the last time you were here, and now you're just a prisoner.

You miss your wings. You miss warmth. You miss the way humans smile when they're happy, when they're nervous, when they're being sneaky, when they realize they've fallen in love with you, and when they're bullshitting the Boyking of Hell to _please don't hurt him I'll do anything you say please just please don't hurt him_.

You miss food. It's not something you missed all those millennia in Heaven because you'd never had it before, but you sure miss it now. The way no two items tasted exactly the same. The way Sam would squirm as you licked whipped cream from his belly. The way Dean would almost come in his pants when you fucked yourself with nothing but pie filling coating your fingers.

You miss the way the sunshine felt on your skin. The way it made you sweat. It was uncomfortable, and it took a while to get used to it, but now that you don't sweat anymore, it's like a missing limb. And you miss watching sweat trail down Dean's back while sweat dripped from the end of Sam's nose onto Dean's already sweat-soaked back.

You miss the way it smelled up top. The leather of the Impala. The gun oil that always seemed to get into everything, and at the time it annoyed you, and you wished you could get rid of it, but you'd give anything to push your nose into Dean's hand and take a big whiff of it.

You even miss the way Sam would fart on long car rides, the air becoming so toxic you'd open the back window and try to hold your breath until Dean gave the all clear signal.

But most of all, you miss the two men you fell for, the men you fought with, the men who hurt you and loved you and frustrated you and loved you and lived and died for you.

The being that walks around Hell as if it's not scared of anything? That's not the Sam who giggled when you kissed his tummy. It's not the Sam who fucked you against the wall. It's not the Sam who knew how to make Dean squeal with just two fingers in Dean's ass and Dean's cock in his mouth.

That's not the Sam who teared up when you said _I love you_ for the first time.

You don't know how long it's been. If you had more of your grace intact you'd be able to tell, but it doesn't matter anymore. You don't even want to look at the things trailing behind you. You refuse to call them wings. You don't have wings anymore because that hurts less than the truth.

A small demon slithers by your cell, the bottom half of it in tatters. You don't have to ask. You know it angered the Boyking and that's why it doesn't have legs anymore. The only reason it still exists is because the Boyking was amused by it.

Yesterday you heard a Hellhound barking, and for just a moment, a brief and glorious moment, you thought it was coming for you. You thought it was all going to end. But then you remembered that Hellhounds _take_ people to Hell. They don't put them out of their misery. They don't give them relief.

You wonder what's left up top. Is everything gone? Or is the Boyking's army going strong, humanity enslaved, rivers running red with blood? Whatever happened, you'll never find out.

You close your eyes because something's hovering around the door to your cell. Whatever it is, it can't be there to save you. It's better not to know. It's better when something just chomps on you, makes you scream in agony, a surprise instead of what you know is coming.

Suddenly you feel warm. You remember what warmth is. You didn't think you'd ever feel it again, but it's unmistakable now, so you open your eyes, and there's Dean, next to you in bed, concern in his eyes, his brow pulled down until he gets that adorable little wrinkle between his eyes. He's saying something, but you're not ready to hear it yet.

Sam's arms wrap around you from behind, and you let out a sigh, your body relaxing even though you're drenched in sweat, your heart pounding. It doesn't matter anymore. You're okay. You're not _there_ anymore, and you're not ever going back.

That thing with the cold eyes and vicious smile hasn't been around for almost six years now, and if Gabriel is to be believed, won't ever be again.

It's Sam behind you. The one who giggles when you kiss his tummy. The one who fucked you against the wall last night while Dean watched and couldn't keep his hand off his dick. The one who made Dean squeal with just two fingers in Dean's ass and Dean's cock in his mouth.

The one who kisses the back of your neck and says _I love you_ for the millionth time while Dean says the same against your lips.

You may not have your wings anymore, but you got so much more in return.


	30. Good Job

**Summary for the Chapter:**

> **Anon Request:** Would you ever consider writing boyking!sam x reader? I wasn't looking for anything in particular I just thought it was an interesting concept and figured it would give you room to run and mold

**Notes for the Chapter:**

>  **Warnings:** Dark Boyking!Sam fic set in Hell
> 
>  **Tags for This Chapter:** Boyking!Sam/Reader, reader insert, torture, violence, rough sex, discussion of off-screen torture of other characters, dark fic, discussion of off-screen non-major character death

You cower in front of him. He's fucking gorgeous, and it you were topside you'd crawl over fifty other people just to ask him out on a date, but he's terrifying, and he's the fucking ruler of Hell.

You don't remember what you did. Back when you were alive you fucked up. A lot. But you're so scared that you can't remember any of it. You must've done something awful because not only are you down here, but you're shivering at the feet of a nightmare.

"I've been told I need to have a meeting with you," Sam says.

You feel his voice inside you. The walls of Hell quake with it, like they're just an extension of him instead of mud and dirt, fire and pain, fear and anger.

You nod, unable to speak. You know it's disrespectful, but you can't make yourself respond other than a quick nod. He's going to kill you, but he'll probably have fun with you first, and you don't want to piss him off.

"Ruby said you were amazing," the Boyking of Hell says. "Said I should see what you can do. Said you'd like to move up in the ranks."

You can't bring yourself to look up at him, but you nod again. Spastic movements that you hope he understands.

"All I see is a quivering mass," Sam says, and then he's crouching in front of you.

The fucking Boyking, ruler of Hell is crouching in front of you. If you were still a human you'd be pissing yourself.

"Ruby never lies to me," Sam says softly, lifting your chin with two fingers.

You're so fucking scared. You don't want to look into his eyes. You don't know what you'll see there. But then you take a quick peek and you can't stop staring. They're beautiful and inviting. They're the prettiest things you've seen since Ricky Keller got behind the wheel after about six shots too many and you thought it was a good idea to get in with him and he ended up killing himself, you, and a family of six on the highway three hundred or so years ago.

"She told me," Sam drawls, "you have a way with weapons and you rival my brother with your skills whenever you've got somebody on the rack."

You can't help but smile. Ruby's proud of you, and if she thinks Sam will like your work, she'd know because she's spent more time with him than anybody besides his own brother.

"Yes, I pick things up quickly," you say, something buzzing in your cold, dead heart.

"Ruby tells me you've broken records around here," Sam says, and the left side of his mouth quirks up into a smile. A smile for you.

You smile for the first time in nearly a century, Ruby pulling the last one from you when she purred in your ear, so proud of your work on that mass murdering son of bitch you broke in less than five days.

"I enjoy my work, sir," you say, and you realize you're not shivering anymore. You're still terrified of him, and for good reason, but he's pleased. You can see it on his face. He wants you. He's going to use you.

"Well, I've got something you might get a kick out of," Sam says and takes you by the hand, leading you somewhere.

You don't ask. One doesn't question the ruler of Hell. He takes you down hallways and around corners. You've never been this far away from your station. You feel the change in the air, the way it feels cleaner, the air easier to breathe, and when the ground gives way to carpet, you hesitate.

"Come with me," Sam says, giving you a gentle tug.

No one has ever said anything about this. Hell is full of rumors and gossip, but you've never heard a peep about this. There's a floral wallpaper covering the walls. It's cheery and blue and white and you're so confused.

You come to a double door that's so tall Sam could carry you on his shoulders without ducking. He throws open the doors and inside is a large room with plush furniture and thick beige carpet and curtains covering windows. And that's what throws you the most. There's light coming in from outside. You're still in Hell. You can feel it. Every demon can. But there's warmth and light and comfort.

"If you're as good as Ruby claims," Sam says, putting his hands on your shoulders and letting you get a good view of the room as he puts his mouth to your right ear, "then I'm going to let you play with him."

You hadn't even seen him until then, and you feel like an idiot for having missed it. If anyone asks, you'll tell them you were distracted by the gaudy curtains. There, on the bed, back to you, hunched over just a bit. But you'd recognize him anywhere. Everyone knows who he is.

"Really?" you ask, just as scared as you are excited.

"He's still mine," Sam says, "but if you can make him scream, I promise I'll make _you_ scream."

You shiver. You really want it. All of it. You want to be good for Sam. You wan to have a crack at the famous Dean Winchester. You want to see first-hand why Ruby always comes back from a night Sam, a devilish grin on her face that lasts for days.

"Thank you, sir," you say.

"Dean," Sam calls out.

"What?" Dean asks, much more grouchy and irritated than you'd expected.

"Playdate," Sam says.

Dean slides off the giant four-poster bed, jeans low on his hips, a worn blue T-shirt that looks more comfortable than anything you've ever worn, and nothing on his feet. He looks vulnerable until your eyes make their way to his face.

"Have fun, you two," Sam says, then he steps back.

Dean stands even taller, defiance oozing from every part of his being. He's eyeing you up like he's going to rip you to pieces and still have enough time to catch his favorite TV program in an hour.

"Let's see what ya got, sweetheart," Dean says, grinning.

You cock your head to the side, not backing down an inch, and you furrow your brow just a bit. "I think I worked on a friend of yours," you say, then pretend to think about it, like it meant nothing, but you're trying to recall small bits of it.

Dean shrugs. "I've known a lot of people."

"Yeah, I guess," you say, casual and uncaring as you take a few steps toward him.

You have no weapons, but that's okay because Dean Winchester is immune to weapons. He's been hurt by the best and he's still here, still holding his head hight. No, you're going to get your time with Sam because you're smart, not just good with a knife.

"He held out for a long time," you say as you circle him, "but in the end he still gave it all up. They all do."

Dean chuckles. "Yeah, when I was working on my own souls down here, it was almost disappointing how easily some of them gave up."

"He begged me to stop," you say, leaning in closer, "even as I pulled out every single one of those pretty feathers."

Dean doesn't say anything, but you can see the slightest little twitch in his left cheek. Just a tiny crack, but you'll take it.

"After he joined me, I taught him how to have a lot of fun," you say. "But it wasn't until then that he told me about every cell, every memory, every quirk that makes up Dean Winchester."

Still nothing. No words from the man who spent his first decade under Sam's rule with a gag in his mouth because he wouldn't shut up. You've seen him by Sam's throne, stubborn stance and eyes burning with anger even though he couldn't speak.

"He's a beautiful demon, Dean," you say. "Maybe you'll meet him again. You wouldn't recognize him, but I think it would be fun to watch him play with you. All those skills he used to fight for you along with all those other skills he learned from me and Ruby and Jo."

Another twitch. Yeah, he didn't know that. Who would have thought she'd be down here? Amusing, really, because she died saving people. Hell is the last place she should've been. Too bad she'd sold her soul just a year before that amazing sacrifice when Ellen was diagnosed. Ellen's not down here, but her baby is, and she's nearly as terrifying as Ruby.

"Oh, that's right," you say, then chuckle, "you know Jo too. Yeah, she helped me tear your little angel right up. She even suggested I take a souvenir."

You wear it around your neck at all times, just because you're proud of your accomplishments. And when you pull it out of your shirt and wave the pretty little feather in Dean's face, his breath catches in his chest.

After the screaming is done and there's blood running down the walls, the bed and other furniture is broken or burned, and Dean's recovering in the corner, Sam takes you by the hand and leads you down another set of hallways and corners and stairways.

He fucks you for weeks, murmuring compliments into your hair, thanking you for your excellent service as he shoves you against the wall and pushes his thick cock back inside you. He does make you scream, just as he promised. You end up tangled in the sheets as he kisses up and down your spine, his cock hard again, his hands strong on your shoulders, your sides, your back as he asks you to to go up top.

"I'd like to see what you'd do with a regiment of your own," he says.

"Thank you," you say. "I'll do my best."

"I know you will," he says as he pushes his cock back inside you, like he can't wait to get back in and take you apart yet again. "Keep it up and you just might sit at my right hand one day."

You moan as he flips you over and plays with you until you can't even remember your own name.


	31. Switching

**Summary for the Chapter:**

> **Anon Request:** I would love to read a story about J2 or Sam/Dean, both are strong characters, no D/s but pure s/m scene/relationship, all consensual, for pleasure of both. Figging, canes, belt spanking/whipping. I hope you'll write it :-)

**Notes for the Chapter:**

>  **Warnings:** None
> 
>  **Tags for This Chapter:** Jared/Jensen, SM, bondage, caning, handjob, paddling, spanking, figging

Jared bends over the sawhorse bench, spreading his legs and grabbing the padded bar they added to the bench for stability. It's custom made, just like everything else in their play room. They're big guys, and they wanted everything to fit just right.

Jensen swishes the cane through the air, checking to make sure it's still pliant and hasn't dried out. He sees Jared out of the corner of his eye, ass on display, in nothing but his black boxer briefs bunched up under the curve of his ass. Jensen's very accurate with the cane, but it's nice to have that added protection.

"Ready?" Jensen asks, adjusting himself with a quick grab at his jeans covered cock, bare feet quiet on the tile floor, the sleeves on his shirt pushed up to his elbows.

"Start with five," Jared says, relaxing his legs, his ass, his back.

Jensen nods even though Jared can't see him and brings the cane down across both ass cheeks. Seconds later Jared squirms a little and groans, a pink line forming across his ass. Jensen hits him again, just below the first strike.

"Harder," Jared says, toes curling as Jensen follows through and gives Jared what he wants. "Yeah, like that. Two more."

Jensen puts two more lines on Jared's ass, the color a darker pink, almost red. "More?" he asks as he brings the cane up between Jared's legs and very gently taps his balls.

Jared goes up on his toes. The boxer briefs aren't enough padding for his sensitive balls, and he lets out a growl. "Dude!'

"Quit your complaining," Jensen says, rubbing the cane back and forth over Jared's balls. "You love it."

"Five more," Jared says.

Jensen immediately pulls back and lets Jared have two more strikes, harder than before. Jared hisses, muscles in his arms tensing.

"Fuck," Jared says under his breath as Jensen hits him three more times, the last one overlapping the very first stripe he'd put on Jared.

Jensen switches the cane to his left hand and reaches out with his right to cup Jared's balls, massaging them through the material.

"Mmm, yeah," Jared moans. "Tap my ass while you're doing that."

Jensen grins as he uses his left hand to start a light rhythm on Jared's ass. He taps the same spot three times, moves on to the next and taps five times before going back to the original spot and tapping seven times.

"Ah, shit!" Jared hisses as he squirms back and forth.

"You wanna come like this?" Jensen asks as he starts tapping in random spots.

"Want your hand on my cock," Jared says.

Jensen brings his left hip a little closer to Jared and transfers the cane from his left to right hand, his left hand reaching around Jared's side and finding his cock already hard. He strokes it a couple times, then brings the cane down across Jared's ass. It's an awkward position, but Jared loves it.

"Yeah, like that," Jared moans. "Mmm, Jay, yeah. Yeah!

Jensen chuckles as Jared comes just like that, shooting so hard he hits the padded bar he's holding onto. The first time Jared comes during a session is always quick, and neither of them really care about stamina anyway because it's all about fun. Jared can come again soon and he'll last longer, but if they don't get the first one out of the way, Jared won't loosen up.

Jared stands up and grabs onto Jensen, kissing him and grabbing his ass with both hands. "You're wearing too many clothes," he says against Jensen's lips.

"Yeah, but you like it when you get to yank my jeans down," Jensen says, grinning.

"You're right," Jared says, giving his ass one more good squeeze before pulling away. "Where do you want me to tie you up?"

"I think I want the overhead rings today," Jensen says.

Jared pulls the padded cuffs from one of the drawers and puts one on each of Jensen's wrists, then buckles each one to the chains hanging from the ceiling. There are two sets, one for Jared and one for Jensen, each at just the right height to keep them on the balls of their feet while playing.

Jensen squirms when Jared crouches down and kisses his exposed tummy, but Jared moves on and unbuttons Jensen's jeans, unzips them, then bends the flaps down.

"Do I need to ask?" Jared says with a smirk.

Jensen chuckles. "No."

Jared nods and grabs a thick paddle off the wall. It's not overly large. The handle is comfortable and the business end is no bigger than Jared's hand, but it's wood covered in leather, which is perfect for Jensen, who prefers thud more than sting. Jared's the one who likes stinging pain.

"Ready?" Jared asks.

"I'd like some bruises," Jensen says, "so don't give me much of a warm-up."

"Mmm, I love when you walk around with my bruises covering your ass," Jared says, then smacks Jensen's right ass cheek.

Jensen moans, adjusting his stance as it forces him forward, his left foot coming off the floor. He spreads his legs a little more and pushes the balls of his feet down, holding on as Jared smacks him again, this time his left ass cheek getting the damage.

"C'mon, Jare, lemme feel it," Jensen says, almost whining. Then the next strike lands, sending Jensen up onto his toes. "Oh, fuck yeah!"

Jared grins and hits him again just as hard. Jensen gets his footing again and grunts with the next strike.

"You ready yet?" Jared asks.

"Oh, I forgot," Jensen says, voice already deeper with arousal. "Yeah. I'm ready."

Jared walks over to the counter top and opens the Ziploc bag, peeling it back around his hand so he doesn't touch the carefully crafted ginger root. He doesn't mind getting it on his hands, but when they're playing it's safer to keep his hands clean in case he touches Jensen's face.

Jared's got the paddle under his left arm, the ginger root in his hand, and he uses his free hand to yank at Jensen's jeans, grinning as Jensen loses his footing with the rough treatment, but when Jared yanks in the front, Jensen's cock bounces out, heavy and leaking. Jared crouches behind Jensen, giving his ass a quick kiss before spreading his cheeks and pushing the tapered ginger root inside him.

"Hey, not so fast!" Jensen complains, squirming.

"What was it you said when I complained?" Jared asks, pretending like he can't remember. "Oh yeah. Quit your complaining. You love it."

"Yeah, yeah," Jensen grumbles, squirming. "Fuckin' burns."

Jared pushes it in until the rim Jensen carved pops inside him and the bulb left outside Jensen's ass is snug, then tosses the bag toward the cabinets. "You want the paddle or my hand?"

"Mix it up," Jensen says, then lets out a yelp as Jared smacks his right ass cheek hard with the paddle. "Yeah, harder."

Jared keeps it steady because Jensen likes to know what's coming, unlike Jared, who likes surprises. He smacks each of Jensen's ass cheeks three times, one by one, then grabs his ass, squeezing the skin, then uses his hand for three smacks on each cheek.

Jensen gets lost in the rhythm, the pain, and the way he can feel Jared's presence in the room like a warm blanket.

Jared builds up the pace, builds up the strength of his strikes, and soon Jensen's moaning, whimpering, and Jared reaches around, grabbing Jensen's cock and stroking him as he uses just the paddle on his ass. It only takes a few strokes and Jensen's coming, body twisting as he lets himself dangle from the cuffs, hips thrusting forward and back.

Jared drops the paddle on the floor, then wraps his arms around Jensen and lifts, getting the cuffs unhooked and lowering them both to the floor.

"Ow, stupid fuckin' ginger," Jensen grumbles as he rolls onto his right hip.

"Big baby," Jared teases as he grabs his discarded boxer briefs and uses them to get the ginger out of Jensen. "Ready for round two yet?"

Jensen chuckles. "My refractory time isn't as good as yours."

"That's okay," Jared says, pinching Jensen's ass and making him laugh. "I don't mind coming a few times while we wait for you to come around."

"Very generous of you," Jensen says. "Hey, does my ass look good?" he asks as he rolls over onto his stomach.

"It always looks good," Jared says, "but yeah, you've got some nice bruising. It'll have some nice blues and purples later tonight."

"Hell yeah!" Jensen cheers. "So what do you wanna do next?"

"Ooh, I wanna do the single-tail!" Jared says, already getting to his feet and heading for the cabinet.

Jensen rolls his eyes and rests his cheek on the floor. It's going to be a long night.


	32. The Name Game

**Summary for the Chapter:**

> **Anon Request:** Could you do a mpregDean with Sam? Dean is nine months pregnant and Sam enjoys talking to their unborn daughter and feeling her move.

**Notes for the Chapter:**

>  **Warnings:** None
> 
>  **Tags for This Chapter:** Sam/Dean, mpreg, fluff upon fluff and nothing but fluff :)

"Daddy's here, sweetheart," Sam whispers as he kisses Dean's belly.

Dean pretends he isn't awake, his eyes still closed and trying really hard not to smile because his little brother is adorable.

"I can't wait to meet you," Sam says, putting his cheek to Dean's belly. "Daddy's gonna take such good care of you."

Dean smiles as their little girl kicks inside him and Sam gasps. Sam's felt it a million times, but the wonder in his eyes and the big smile that breaks out on his face nearly kills Dean every single time.

"I came up with a few more names," Sam says. "I'm gonna run them by you first because your papa's being an asshole and shooting down every suggestion I make. So if you like any of these, give me a good kick and I'll tell papa you think those names are really cool."

Dean's chest aches. It's so cute. It's so adorable. He had no idea Sam would be like this. Sure, Dean likes kids. He talks to them like they're little versions of adults instead of a tiny creature. He loves the way they look at the world. He feels protective of them even when they're not his.

But Sam. Well, Dean's never seen him interact with kids much, and when he first realized he was pregnant he actually worried about it. They hadn't been trying to get pregnant, but Dean knew Sam was open to the idea. If Dean had known Sam would turn into a daddy within just a week of hearing the words "we're having a baby," Dean would've already had a little one running around and they'd be on their second.

"Haley, Clarissa, Danielle, Bonnie, Laura," Sam says, giving the baby time to kick in between each name. "Riley, Kara, Willow."

Dean really hopes their little girl doesn't kick on a name he hates. He's had his heart set on Lana. He's wanted it ever since he got hooked on that Smallville show. Lana was so pretty, and of course he likes Batman better, but he can't imagine naming his little girl Barbara. He's already been calling her Lana when Sam's not around.

"Sonja, Britney," Sam continues, but then he pauses longer and lets out a sigh. "I suppose I gotta give you Papa's favorite name too. Just to make this fair. What do you think of Lana?"

The baby kicks and Dean can't take it. He starts laughing, his belly jumping, shoulders, shaking. He opens his eyes to see Sam glaring at him.

"Oh, c'mon, Sammy, that was funny and you know it," Dean says, holding his stomach because he's laughing so hard.

"How did you do that?" Sam asks, frowning down at Dean's belly.

"It's probably because I've already been calling her that," Dean says. "Babies can hear you even in the womb, and she's gotten used to hearing me call her Lana."

She kicks again and Sam rolls his eyes. "Okay, fine. We'll name her Lana. After Superman's girlfriend," he says, and mostly he's teasing, but Dean can hear just a little bit of excitement in there too.

"Really?" Dean asks.

Sam nods. "You really like it. And if she likes it too, then you both get what you want," he says, a smile tugging at the corners of his mouth.

"Already spoiling us," Dean says.

"I actually like the name," Sam admits, blushing a bit as he caresses Dean's stomach. "I was just giving you a hard time because you're a geek and I've gotten enough teasing from you over the years I gotta get you back."

Dean grabs the back of Sam's neck and pulls him in for a kiss. "Did we just name our daughter?" he asks, unable to wipe the grin off his face.

"Yeah, we did," Sam says, his left hand going to Dean's stomach and rubbing it again.

"Now we just have to come up with a middle name," Dean says, then chuckles when Sam sighs dramatically and flops his head down on Dean's chest.

"It's a good thing Lana's going to be really, really cute, otherwise this would be too much work," Sam says wistfully.

"Dude, babies aren't cute when they first come out," Dean says, wincing. "You know that, right?"

"You said I was cute," Sam says pouting at Dean. "Of course she's gonna be cute!"

"Nah, you were fugly for the first two weeks," Dean teases. "All red and blotchy. I didn't even wanna hold you!"

"You're lying," Sam says, lifting his head to grin at Dean. "I may have been fugly, but Dad said you wouldn't stop bugging him about holding me."

"Yeah, that's the thing about babies," Dean says, running his fingers through Sam's hair. "It doesn't matter if they're fugly or the prettiest baby in the world, they're yours and all you see is your amazing kid."

"She's gonna be amazing," Sam says, rubbing Dean's belly. "Aren't you, Lana?"

Sam gasped as the baby kicked again.


	33. Never Gone

**Summary for the Chapter:**

> Anon Request: Hey, I really love your fics! I'd like to request one, if that's okay? I was thinking Wincest with demon!Dean (doesn't have to be MOC version) still being super protective of Sam? Maybe after a hunt where Dean rescued him and Sam could tell how much Dean cared, Sam decides it's time to try sleeping together again? At some point during the sex Dean gets carried away and is too rough with Sam and almost hurts him and he's horrified but Sam understands and coaxes him through it?

**Notes for the Chapter:**

>  **Warnings:** None
> 
>  **Tags for This Chapter:** Sam/Dean, MoC!Dean, rough sex, fucking/anal sex, biting, manhandling, minor blood

Sam hasn't touched Dean since the Mark. Not like he used to. He's not scared exactly, but he wonders if this is how Dean felt when Sam was soulless. It's Dean but it's not Dean. And Sam doesn't really know what to make of it. So he keeps that buffer between them.

Until Dean tears apart a demon right in front of his eyes. Dean rips the limbs off because it had shoved Sam across the room. And that's the first time Sam sees his brother in there, sees the man he died and lived for.

Sex was always frenzied and intense after a hunt, but when they get back to the bunker Dean's gentle, making sure he's okay, insisting Sam take off his shirts so Dean can look at his back, right where the chair rail hit him.

Sam holds his breath as Dean's hands, gentle and rough at the same time, push him this way and that, prodding, and when Dean's finally satisfied that Sam's okay, he cups Sam's face, opens his mouth like he's about to say something, but then turns and starts to leave.

"Wait," Sam says.

Sam's stomach clenches when Dean turns around, because it takes Dean a moment to recognize the look on Sam's face, but when he does he's heading for Sam with a purpose. Sam backs up a step, because Dean can be intimidating even when he doesn't have the Mark burned into his arm.

He's still not scared, just cautious. But then Dean's kissing his collarbone and wrapping his arms around Sam, pushing him back against the wall even as he repeats "Sammy" over and over again, lips grazing Sam's chest, his shoulder, his neck.

Sam curses under his breath and surges forward, backing Dean toward the bed. Dean doesn't fight him, doesn't try to get the upper hand, and soon they're tangled on the bed, kissing like they haven't touched in years instead of months.

Dean turns Sam onto his stomach and pulls the jeans and boxers down just enough to spread Sam's ass cheeks and spit on his hole. Sam moans, pushing back, wanting more.

Sam fumbles around under his pillow and grabs the lube, then tosses it over his shoulder. Dean catches it, then there's cold lube being pushed into his hole. Sam gasps and squirms, wants it so bad, can't wait.

"C'mon, c'mon," Sam says through clenched teeth, then chuckles as Dean flips him over again. "Ah, fuck," he hisses as Dean sinks into him, pushing Sam's legs toward his chest.

Dean fucks him even as he pulls Sam's boots, jeans, and boxers off and throws them across the room. Dean's still fully clothed, his jeans rough against Sam's ass, his balls, but it only makes everything better.

Sam grunts as Dean drops down onto him, moans into Dean's mouth as Dean shoves his tongue into Sam's mouth, holding his head with both hands as he licks and bites at Sam's lips and tongue.

It's overwhelming in the best way, and Sam doesn't know why he kept his distance. He missed this. Missed Dean. But Dean's right here.

"Ah, fuck!" Sam yelps as Dean bites down on his shoulder. It hurts. A lot.

Dean pulls back, eyes wide and blood on his lips. He meets Sam's eyes and winces. "Shit, Sam, sorry. Got a little carried away."

"It's okay," Sam says. It's not the first time he's been injured while fucking. If Dean knew half of the shit he and Ruby did.

"Sam, I don't know if I can-"

"You won't hurt me," Sam says. "C'mon, fuck me."

"I can't control th-"

"Fuck. Me," Sam growls, grabbing Dean's shoulders and pulling him back down for a bruising kiss, wrapping his legs around Dean and pushing on his ass with the heels of his feet, encouraging him to get back to fucking.

Dean does. He fucks Sam hard, panting and biting and rough and it's just what Sam wanted, what he should've known he could have all along.

By the time Dean comes deep inside him, Sam's already come without either of them ever touching his cock, belly wet with his release. Dean collapses on him, panting onto Sam's neck.

Sam chuckles when just minutes later Dean's hips start moving again. Dean never had a very long refractory period, but nothing like this. Sam figures they have lost time to make up for and settles in for round two.


	34. Before

**Summary for the Chapter:**

> Anon Request: For the Tumblr Ask Box requests I saw on AO3, maybe Cas likes Dean to be real clean before their more intense/longer scenes so makes sure to shower/shave him etc beforehand, and he's all gentle about it, sort of like aftercare but beforehand and likes to include an enema or two just to make sure Dean is squeaky clean before their scene?

**Notes for the Chapter:**

>  **Warnings:** None
> 
>  **Tags for This Chapter:** Dean/Castiel, enema, shaving, fluff, no sex

Dean didn't like it. At least not at first. He didn't see the point. Sex was sex, which he really liked, but getting cleaned out and prepared? No. That was done in private and why would anybody else be interested in that?

"Almost done," Cas says as he wipes the hair and shaving cream off the razor.

Dean's spread out on the bed, naked with a towel beneath him, legs wide with Cas kneeling between them as he gently cleans all the hair away from Dean's crotch.

But that's just it. Dean's never had anyone do this for him. He's never had anyone interested in it. But Cas loves it. Cas takes his time, using soft touches and soothing words, all while Dean gets pampered. And it wasn't until Dean finally let him do it a time or two that Dean realized just how much he enjoyed it.

Sure, it was mostly for Cas, but Dean liked the attention, the clean shave, the very thorough moisturizing Cas would do so Dean wouldn't get ingrown hairs, and the way Cas would talk to him while he was doing it.

"Are you too cold?" Cas asked.

"No, I'm good," Dean said. 

Cas didn't talk a mile a minute, and he didn't really say anything of importance, but the softly-murmured words coming from Cas were soothing and relaxing and everything Dean didn't know he wanted.

Dean moaned as Cas wiped him clean with a warm washcloth. Nothing was ever cold. Cas always used warm water, warm lube, warm tools, and he'd even warm the razor in his hand before using it on Dean.

"Roll onto your side," Cas said, mostly rolling Dean into position himself. "Relax for me."

Dean was totally relaxed. Cas didn't need to tell him. Cas spread his ass cheeks and lubed up his hole before gently pushing the tip of the enema hose into him.

"I'm starting the water now," Cas said.

Dean closed his eyes as he felt the water flow into him. It wasn't shocking because it was warm, and he didn't really feel it other than a sense of fullness that was getting more intense as Cas filled him up.

"You're going to keep it in for three minutes before I help you to the toilet," Cas said.

"Okay," Dean said, smiling as Cas leaned down and kissed Dean's hip.

"Any cramps?" Cas asked, hand trailing over Dean's stomach.

"Not yet," Dean said.

Cas gently massaged Dean's stomach with his left hand while holding the enema tube with his right. Dean hissed as the first cramp hit, and Cas eased back on the flow of water. Dean couldn't feel how fast it was coming out of the tube, but he knew Cas well enough to know that Cas had rolled the little wheel forward, closing off the tube so only a trickle of water was running into him, giving him a chance to adjust to the water.

"Is it better yet?" Cas asked.

"Yeah," Dean said, nodding.

Cas rolled the wheel backward, the flow of water increasing and soon enough Cas patted his hip.

"Squeeze. I'm going to take it out now," Cas said.

Dean did as he was told, and managed to hold the water as Cas pulled the tip out of his hole.

"Time starts now," Cas said, fingers trailing over Dean's skin, always touching, always caressing.

Kisses down his spine, over his hip, along his side, down his arm, and even the tips of his fingers are kissed. Dean doesn't remember when this became something he craved or even allowed in the first place, but he doesn't know what he'd do without it anymore. What he'd do without Cas.

"Time's up," Cas said, climbing off the bed and helping Dean up. "We'll take a shower, get all clean before I make you all messy again."

If someone had told Dean a few years ago that subspace could be found without pain, he wouldn't have believed them. But as he sits down on the toilet, quiet and obedient, letting Cas stroke his hair, murmur encouraging words, and kiss his forehead, Dean forgets about everything else for a while and just lets Cas worry about it for him.


	35. Longing

**Summary for the Chapter:**

> Anon Request: If you ever find yourself not busy with requests, might I impose? I would love to see some crobby mpreg with pregnant bobby. Perhaps Crowley makes a deal with him in Hell that he can have free reign, if he'll bear Crowley's children? But it's consensual on Bobby's part. Ta!

**Notes for the Chapter:**

>  **Warnings:** None
> 
>  **Tags for This Chapter:** Kinda sorta implied Bobby/Crowley, mpreg, grumpy!Bobby, fluff, cravings, moodiness/hormones, crying

Bobby struggles to get up from his chair, ignoring the way Dean and Sam tense, as if they want to get up and help him. The other fifty times he barked and snarled at them has trained most of that out of them, but they're gentlemen, were raised up right, and all Bobby's snarling doesn't take that away.

He finally gets himself up and waddles into the kitchen. He stares longingly at the beer for a moment, not for the first time wondering if a half demon child would be affected by alcohol. He needs to ask Crowley, if the idiot would show up.

Bobby grabs a bottle of juice and opens it, then waddles back into the living room just in time to see Sam and Dean pull a gun on Crowley.

"Hey!" Bobby growls, satisfied when the boys flinch. "Down!"

"It's for the mum to be," Crowley says, holding up the large basket of goodies.

"Wait, what?" Bobby says, scowling at Crowley.

"Are you getting enough rest, sweets?" Crowley asks, and damn it but he looks concerned.

"You can knock that right the hell off," Bobby says, then nods toward the basket. "Now what's that?"

Crowley reaches into the basket and holds out the most disgusting thing Bobby's ever seen. It's purple and blue and yellow and there are spikes on it. It's about the size of an apple, but Bobby swears he sees it jiggle.

"I'm already carryin' yer kid," Bobby grumbles, "so you can just forget about shoving anything else in me."

Crowley deflates a little, and the look on his face seems like it might be hurt. "You really think I'd do anything to upset you?"

Bobby shrugs. "Dunno."

"This," he says as he holds up the thing in his hand, and yes, it does jiggle, "is a gijbyarngn and it'll settle your stomach as well as fill that craving you've had for a beer."

"Huh?" Bobby says, confused and a little disgusted.

"You wanted alcohol," Crowley says. "In fact I specifically recall you wanting me to bring you a beer when you asked me to come here."

Bobby turns to Dean, then Sam, eyes wide. "If you breathe a word about any of that longing shit or ever mention this again, nobody will ever find your bodies. Understood?"

Dean and Sam both nod, backing up a step.

Bobby reaches out and snatches the thing from Crowley's hand. "What do I do with it?" he asks.

"It's like fruit," Crowley says. "Take a bite out of it. It's good."

Bobby sniffs it, not quite as disgusted when the thing has a sweet scent. He takes a bite and immediately decides he wants more of them, moaning as he chews.

"I brought four of them," Crowley says proudly. "I'll get you more if you want."

Bobby flops down onto his easy chair and slurps some of the juice from his lips. Dean and Sam slowly lower themselves to their chairs, watching Bobby with a morbid fascination.

"What else ya got?" Bobby asks, gesturing toward the basket.

Crowley puts the basket down on the floor in front of Bobby and pulls out a jar of something bright green. "This will help with stretch marks."

Bobby scowls at him. "What makes you think I give a fuck about that?"

"Its other properties include a gentle warming effect and a very pleasant smell," Crowley says.

Almost as if Crowley had reminded him, Bobby shivers. He _has_ been cold ever since he started showing. He thought it was hormones.

"The baby doesn't like to be cold," Crowley says, "and your body temperature is lower because you're working at growing our child."

" _Your_ child," Bobby mumbled with a mouth full of fruit.

"Well, see, here's the thing," Crowley said, rummaging through other items in the basket and pulling out a tall glass bottle. "He's got your DNA too, and that's why I brought this."

Bobby takes a whiff of the clear substance in the bottle as Crowley waves it beneath his nose. He smells cucumber and melon and lets out a soft moan because it's his favorite bubble bath.

"This will calm him down if you're having trouble getting to sleep," Crowley says, then caps the bottle and puts it back into the basket.

Bobby ignores the snicker from Dean. He really deserves it after all the teasing he's given the kid all these years about his love of showers and smelly soaps.

"What else ya got?" Bobby asks, but frowns when Crowley pulls out a bag of white chocolate. "I'm not a chocolate kinda guy."

Crowley chuckles. "Females develop slower at first, but once they do come into their own, they'll give you stronger cravings than males. You'll be needing this."

Bobby's eyes widen. "Excuse me?"

"You didn't know?" Crowley asks, puzzled expression on his face.

"You put _two_ of these things in me?!" Bobby asks, struggling to get up, then giving up and just glaring at Crowley.

"No," Crowley says. "They're identical twins, not fraternal. A boy and a girl."

In the three months Bobby has been pregnant, he hasn't really thought of the baby as his. He hasn't even thought of it as a baby. He made a deal with Crowley and has been carrying something for him, that's all. Even when Crowley started calling the baby "he" it didn't really hit him, but for some reason the fact that Crowley says twins, it finally hits him.

Twins. They'll look alike. They'll be two beings he's helped create and grown inside himself. And if the boy likes the same bubble bath and the girl already is developing cravings for white chocolate, they're real.

His eyes well up with tears as he takes the chocolate from Crowley. His bottom lip quivers and he doesn't even bother trying to hold it in. He doesn't give a fuck what Dean and Sam have to say about it. He's got two babies in his body, and he'd almost given in and had some beer, almost hurt them.

"Alcohol doesn't hurt them, love," Crowley says softly.

"I didn't even know," Bobby whispers, tears running down his face. "I'm a shitty father who doesn't even know that his kids can handle alcohol."

Crowley crouches down and puts a hand on Bobby's knee. "You're a wonderful father who chose not to drink alcohol so he didn't hurt his children, whether you knew it would or not."

Bobby sniffs and opens the bag of chocolate, shoving one in his mouth and chewing loudly as he sniffles and wipes at his face. It tastes amazing, and it's exactly what he didn't know he wanted.

"Thanks," Bobby says to Crowley.

"Anytime, sweets," Crowley says. "I mean it. Any time you need me. No matter what. Just think about me and I'll come."

"Okay," Bobby says and shoves another chocolate in his mouth.

Crowley's suddenly gone and Bobby's left with two wide-eyed guys frozen in their chairs. Bobby holds the bag of chocolate close to his chest just in case the Winchesters have any ideas about taking it.

"Well, what are you waiting for?" Bobby grumbles, wiping at his eyes with his free hand. "Beer me!"

Sam and Dean nearly kill each other as they both scramble to be the first out of the living room and into the kitchen.

Bobby grins at he takes another piece of chocolate out of the bag and pops it into his mouth, the babies inside him content for the time being.


	36. Bottles and Baths

**Summary for the Chapter:**

> Anon Request: Can you please write a non-sexual infantilism of baby!sam, daddy!dean and daddy!cas please?

**Notes for the Chapter:**

>  **Warnings:** None
> 
>  **Tags for This Chapter:** No obvious pairings, but Dean/Castiel if you want to read it that way, non-sexual infantilism/age play, diapers, baths, fluff, bottles, baby!Sam, Daddy!Dean, Daddy!Castiel

Daddy makes him a warm bottle downstairs while Papa gets his bath ready upstairs. Sam chews on his fist as he waits patiently, naked on the bathroom mat and peering into the tub. Papa knows just how much bubble bath to put in, and Sam grins as Papa adds some toys to the water.

"Uh?" Sam grunts.

"C'mon, kiddo," Papa says as he picks Sam up and settles him in the water before kneeling just outside the tub.

"Fishy!" Sam says, holding up his squeezy fish.

Papa smiles, green eyes sparkling with love and amusement. "Yeah, that's your fishy. Did you see what Daddy got you?" he asks as he points to the corner of the tub enclosure.

Sam gasps when he sees it. "Puppy!" he nearly squeals, reaching out and grabbing his new squeazy toy and hugging it to his chest.

"Don't forget to say thank you to Daddy when he comes up here," Papa says.

"'K," Sam says, then introduces his puppy to his fishy.

Papa picks up the shampoo and starts to wash Sam's hair. Papa's better at it than Daddy is because Daddy's been doing it for much longer. Daddy even did it back when Sam was a baby, not a big boy like he is now. Papa never gets the soap in his eyes even if Sam's playing with his toys.

"Head back, Sammy," Papa says.

Sam does as he told and squeezes his eyes shut because you can never be too careful. Papa rinses Sam's hair, then gives Sam a kiss on the top of his head to let him know he's done.

"Good boy," Papa says, then grabs Sam's turtle squeezy toy and uses it to kiss Sam's neck, making kissy noises.

Sam giggles, putting his chin to his chest because it tickles when Papa does that. Sam holds his new puppy up to Papa's cheek and makes kissy noises as he touches the puppy's face to Papa's skin.

Papa gasps. "I get puppy kisses?" he asks, smiling.

"Yeah," Sam says, nodding.

"Your bottle's ready, little one," Daddy says from the doorway, holding the bottle up.

"You hungry, kiddo?" Papa asks.

"Uh-huh!" Sam says, nodding, then he holds up his new toy and smiles at Daddy. "Tank you."

Daddy grins. "You're welcome."

Sam gives his new puppy and his fishy each a kiss before setting them on the edge of the tub. Papa unplugs the drain and Sam holds his hands up in the air as the water goes down the hole.

"There's our big boy," Papa says, wrapping a fluffy towel around Sam and lifting him out.

Sam snuggles up to Papa. Papa's strong. He can carry Sam around the house. Daddy can too, but that's because he's got special stuff inside him that makes him look pretty and glowy when anything outside the house gets scary.

Papa sets Sam down on the changing table and gets him into a diaper while Daddy picks out some pajamas.

"How about these?" Daddy asks, holding up some pajamas that are white with blue and yellow stars all over them.

"Yeah!" Sam says.

Papa puts his pajamas on, then lifts him off the table. "Okay, Daddy, sit down and I'll put Sammy on you for his bottle."

Daddy sits down on the sofa, scooting to one side so Sam's butt can rest on the seat while his head is cradled in Daddy's lap. Daddy holds the bottle up for him and runs his fingers through Sam's hair while Papa sits down on the other end of the couch and puts Sam's legs over his lap.

Sam closes his eyes, happy and content as his Papa and Daddy both gently caress him and Papa tells a story about fairies and space ships and corn fields. Sam's asleep before they put him into his crib.


	37. The One Where You Do That Thing

**Summary for the Chapter:**

> **[Assbuttintheimpala's Request](https://archiveofourown.org/works/4244124/comments/38633255):** Could you do marine!Dean who has been deployed overseas for a while and he surprises his boyfriend twink!castiel with a visit. Rough, needy welcome home sex would be amaze Bottom!Cas too please with any other kinks you like :) Thanks heaps!

**Notes for the Chapter:**

>  **Warnings:** None
> 
>  **Tags for This Chapter:** Marine!Dean/Twink!Cas, AU, manhandling, fucking/anal sex, blowjob/oral sex, dirty talk, discussion of DP and toys

Cas didn't know he was coming home, and Dean grins as he sneaks up behind the kid and wraps his arms around him.

"Dean?!" Cas screams, dropping the plate he'd been washing on the floor.

Dean doesn't care. He carries Cas to the bedroom, soap suds and all, Cas giggling the whole way. He doesn't even make it to the bed, just yanks the pajama pants down, lets them fall to the floor as Cas wraps his legs around Dean.

"Missed you," Cas says, kissing Dean's nose, his cheeks, his forehead. "Missed you so fuckin' much."

"Missed you more, baby," Dean says, then moans as he pushes a finger into Cas' hole and finds him wet.

"I was playing with myself," Cas says, the blush of his cheeks betraying the cocky smirk.

"Were you thinking about me?" Dean asks as he pushes his cock into Cas and ruts up against him.

Cas' head smacks into the wall as he whimpers, adjusting to a cock that's bigger than the toy he was playing with. "Yeah. I came watching that video you made for me."

"Which one?" Dean asks, because he'd left about five of them, not including the ones he's made for Cas over the last two years they've been together.

"The one where you look right into the camera," Cas says, fingernails scratching at Dean's shoulders as he rolls his body, trying to get Dean deeper inside. "The one where you do that thing."

Dean laughs. "Oh, that one," he drawls, teasing. "Totally narrowed it down for me."

Cas scowls at him. "How'm I s'posed to think with that big cock in me?"

Dean nibbles on Cas' pouty lip, then carries him over to the bed and tosses him down.

"Hey!" Cas yelps, still in his T-shirt, cock hard and leaking.

Dean climbs onto the bed and grabs Cas around the waist, turning him around and sitting Cas down on his cock as Dean kneels. Cas groans, arching his back and reaching up to cradle Dean's head, the position accentuating Cas' little tummy.

"The one where you used that clear fleshlight," Cas says, trying to fuck himself on Dean's cock. "You had the camera on the nightstand and you were holding the fleshlight down on the bed, fucking it while you looked at me through the camera."

"Oh, yeah, that one was fun," Dean says, wrapping a hand around Cas' cock and stroking as he fucks Cas.

"Mmm, yeah, and you were talkin' dirty to the camera," Cas says, wriggling against Dean. "Tellin' me that thing you wanted to do to me."

"That thing I still haven't done to you yet?" Dean asks, grabbing Cas' wrists and placing Cas' hands on the headboard.

Cas takes the hint and grabs on hard. "Yeah. We still gotta do that," he said, breathless.

Dean wraps his hands around each of Cas' thighs and yanks him back, fucking Cas so hard that Cas' knees don't even touch the bed. "Need to work up to it," he says.

"Yeah, my hole's too small for that," Cas says. "Your cock's big. I can't even imagine what it would feel like to have two of them in me."

"I bought the kit on the way home," Dean says.

Cas also doesn't know about the other toys Dean bought on the way home, and he has a feeling Cas is going to scream his name when he slips the vibrating cock ring onto Cas while he pounds into him from behind.

"Fuck yeah! Can't wait to try that!" Cas cheers, body nearly shaking with excitement. "How long do I get you?"

"Two weeks. Two long weeks of fuckin' you on every surface of this house," Dean says, then groans as he comes inside Cas, fucking him so hard the headboard bangs into the wall over and over again. "Gonna spend more time inside you than not. Gonna fuck you the whole two weeks," he says as his hips slow and he pulls Cas away from the headboard, flopping back, Cas landing on top of him as they pant.

"Hey, you're not done yet," Cas grumbles as he squeezes around Dean's cock.

Dean chuckles as he pushes Cas off him and gets to his knees. Cas cries out as Dean sucks him down, fucking up into Dean's mouth as Dean grabs his ass and doesn't stop until Cas is coming down his throat, screaming and thrashing about.

"Missed you so fuckin' much," Cas slurs.

"Missed you too, baby," Dean says as he wraps his arms around Cas and settles in for a little nap before round two.


	38. The Sniffles

**Summary for the Chapter:**

> **[Anon Request](https://archiveofourown.org/works/4244124/comments/40491367):** I have a kink for sneezing/illness/caretaking. I would like something with Sam/Dean where Sam gets off on Dean's sneezes. Or, honestly I would SERIOUSLY be just as happy with Sam getting off on just Dean being sick, minus the sneezing. Just like kitten-weak sick Dean and Sam... taking care of him. Sam should want to make him feel better but you can have him tease Dean or go a bit dubcon if you want with it too since Dean would be sick/kind of out of it, just no completely evil!Sam please.

**Notes for the Chapter:**

>  **Warnings:** Uhm, bodily fluids?
> 
>  **Tags for This Chapter:** Sam/Dean, sick!Dean, sneeze kink, sickness/illness kink (Dean has a cold), masturbation, bodily fluids, cuddling, somnophilia (kinda), blowjob with very slight dub-con only because Dean’s so out of it
> 
>  **A/N:** I had a lot of fun writing this. Sneeze kink is something I forget about until I read something about it, and then I remember how much I like it, so thank you, anon :)

*heh-choo-eurg*

It ended on a moan, and Sam smiled, because Dean never did handle being sick well. Most people were more vulnerable when they were sick, but with Dean it was like he just let his walls come crashing down.

Sam figured that was part of the reason why he found it such a turn-on. Dean never put down all his walls, very rarely let people see the real him, and yet Sam got to see that part of Dean.

*he-ach-achoo*

Sam had already given Dean some cough and cold medicine, had fed him soup even though Dean whined about the lack of "real" food, and he'd wiped Dean down while his brother whined about how cold he was.

Dean turned over in bed and threw his left arm and leg over Sam. Sam felt that swell of emotion in his chest as Dean grunted and put his his head down on Sam's upper arm. Dean was too out of it to realize he was cuddling in bed, and even if he did he might not care because he was so sick.

*eeeachoo*

Sam's eyes widened and his cock twitched in his boxers. Dean had to be sleeping because he hadn't even tried to cover his face. Dean was a dead weight on him, little puffs of his breath ghosting over Sam's shoulder, cooling the snot he'd just sprayed over Sam's skin, and Dean was completely comfortable.

Dean made a little noise of snuggled closer to Sam, holding Sam tighter. Sam waited a moment to make sure Dean was out and reached down with his right hand, slowly reaching into his boxers. Dean's breathing was a little rough, but the medicine was doing its job because he sounded less congested than he did earlier.

Sam wrapped his hand around his hard cock and stroked himself, turning his head and pushing his nose into the hair at the top of Dean's head. Dean's hair was sweat-soaked, and Sam decided to get Dean into the shower once he'd had a chance to nap.

His cock was leaking, balls aching he was so turned on. He placed a kiss on the top of Dean's head and shivered a bit as Dean let out a happy, contended little moan.

Sam stroked himself faster, hoping he wouldn't disturb Dean. Dean sniffled, and just as Sam picked up the pace again, Dean sneezed, wet and loud. Sam came quietly, biting his lip and squeezing his eyes shut, toes curling as he forced himself to stay still.

"S'mmy," Dean moaned, "don'feel good."

Sam rubbed his nose in Dean's hair and gave him another kiss on the top of his head. "Go back to sleep, Dean. I gotcha."

Dean wasn't really awake. Not really. And as soon as Sam spoke, Dean was already settling deeper into sleep. Sam pulled his hand out of his boxers and licked himself clean, wiping the last of it on the sheets.

He settled in, closing his eyes, the too-warm weight of Dean against him soothing. Dean snuffled, then coughed and let out a moan. Sam fell asleep with his nose still in Dean's hair.

The cough medicine wore off quickly, and soon Dean was coughing and hacking again, waking the both of them up.

"You're going to make yourself throw up," Sam said as he held the little cup to Dean's plump lips.

"Don't want it," Dean whined, turning his head.

"C'mon," Sam said, cupping the back of Dean's head and holding him still while he pushed the plastic against Dean's lips.

Dean moaned and tried to push Sam away, but he was in no condition to fight it and eventually just drank the medicine. "Ugh, disgusting," he grumbled as he pushed his face into the pillow.

Sam chuckled softly as he rinsed the cup out in the sink and got back into bed. Dean was still coughing.

"Calm down," Sam said, running his fingers through Dean's hair. "If you throw the medicine up I'll have to give you more."

Dean let out a whine, which only made him cough more. He coughed so hard he gagged, and Sam knew he had to do something.

"Okay, let's try this," he said as he pulled his cock out and got to his knees.

Dean blinked at him for a moment, eyes a little unfocused, confused and not really getting it at all.

"Open your mouth," Sam said, pushing his thumb into Dean's mouth.

Dean did as he was told, but as Sam pushed his cock into Dean's mouth, Dean started to cough again. Sam hissed, the sensation of Dean coughing around him only turning him on more.

He wasn't trying to hurt Dean, so he pulled back and pushed in again, giving Dean some time to breathe. Dean's eyes widened and he pushed at Sam, sucking in a deep breath before sneezing all over Sam's stomach.

Dean whined around Sam's cock, closing his eyes and relaxing as Sam pushed in and pulled out, over and over again, giving Dean something to concentrate on.

"There ya go," Sam said, wiping the tears from the latest coughing fit from Dean's cheeks.

He didn't bother to wipe the snot from under Dean's nose. Dean didn't seem to notice and Sam certainly didn't mind. Dean moaned around him, then choked again, right hand coming to rest on Sam's thigh. He wasn't pushing Sam away, and Sam suspected it was just because Dean was so clingy when he was sick, needed more and more physical contact to the point where even now, with Sam's cock in his mouth and Sam's hands cupping his face, Dean still wanted more.

Sam wasn't going to last long. Dean was making snuffly noises, his nose was running, and he was relaxing more and more as Sam fucked his mouth, letting Sam do whatever he wanted.

Dean didn't try to pull away the next time he sneezed. Sam backed off enough that Dean could get some air, almost coming as Dean's snot sprayed onto Sam' cock, ran down his upper lip, and the drool from Dean's mouth started to drip down onto his neck.

Sam wasn't moving very fast. Didn't need to. Just kept up a steady pace so Dean could breathe. Dean started another coughing fit and Sam pushed Dean's mouth closed around his cock. Dean tried to twist away, more drool and snot running down his face, but Sam just held him. Sam pushed his thumbs into Dean's mouth on either side of his cock, and Dean sucked in a lungful of air before sneezing again.

"Oh, fuck," Sam moaned, his cock dripping with spit and snot as he came down Dean's throat, those plump lips lax around Sam's cock.

Dean just swallowed it down, as if it didn't make a difference to him whether it was more of his own spit or Sam's jizz. Sam pulled out and yanked his own shirt off, using it to clean his cock and stomach before wiping Dean's face clean.

Sam tossed the shirt onto the floor and snuggled down with Dean, who was already snoring, his coughing fit over since the medicine had a chance to do its job. He drifted off wondering if Dean's asshole would clench around him if Dean sneezed while he was fucking him.


	39. A Lasting Impression

**Summary for the Chapter:**

> **Anon Request:** Can you write a one-shot where Dean spanks a human, ex-angel canon Cas? Its long and merciless and A long time coming, until it's over--then it's all comfort and fluff. No sex.

**Notes for the Chapter:**

>  **Warnings:** None
> 
>  **Tags for This Chapter:** Discipline spanking - Dean spanks Cas, non-con spanking, harsh spanking, crying, begging, and a good dose of fluff, talk of parental spanking (John + Dean). This is genfic, but squint and you could call it Dean/Castiel :)

He's faced down demons. The King of Hell. Powerful witches. He's been alive longer than the human who's driving twenty miles over the speed limit and hasn't spoken to him in nearly forty-five minutes.

Even Sam's quiet. He must feel the tension.

Cas feels shaky, and he doesn't understand why. Sure, he's fairly certain he won't enjoy what's about to happen, but it's not the worst he's experienced. Not even by a long shot.

_"You even think of doing something this stupid again and I'll throw you over my knee and beat your ass until it's black and blue."_

Cas closes his eyes and tries to control his breathing. Of course he knows what a spanking is. He may have done something stupid, but _he_ isn't stupid. And really he had good intentions.

As he stares out the rear passenger-side window, he wonders how many humans have been in this same situation. Good intentions don't always mean it was the right thing to do.

He wonders if, now that his grace is completely gone and he's one hundred percent human, he's going to make more and more mistakes.

Dean pulls up outside the bunker and shuts the car off. Cas wants to hold his breath, and if he had his grace he could, but he can't, and he doesn't want to move, doesn't want Dean to notice him, because as big and bad as Cas was just months ago, he's not anymore, and it's terrifying and thrilling at the same time.

"Get him some new clothes," Dean says as he pulls out his wallet and hands Sam two hundred-dollar bills. "And pick up something for dinner. Something he can eat while standing."

Cas' breath catches in his chest and his stomach clenches. He doesn't know why his body just does it. He knew what was coming, but the way Dean's talking about it, like he assumes Cas won't be able to sit, and like Cas needs his clothes purchased for him, well, it's unsettling. Cas doesn't suspect Dean's using scare tactics. He's not that kind of guy when it comes to things like this. But it's still making his palms sweat, and he can't figure out if he wants to open the door and make a run for it or never move again.

"Dean," Sam says.

It's a warning. Cas can hear it in Sam's voice. Even though Sam's just as upset as Dean over this whole thing, Sam's worried about him. It's another aspect of this whole thing Cas hadn't anticipated, and the backs of his eyes ache and burn. His nose tickles a little bit.

"Don't start," Dean hisses, then opens the door and gets out.

Sam slides over into the driver's seat, and even though Cas knows he should be getting out, he can't make himself move. He's frozen and he wonders if his lungs might even freeze up. He flinches as his door opens.

"C'mon, let's go," Dean says, holding the door open for him.

Cas is looking forward, eyes on the back of the seat in front of him. He can't move. He doesn't know why, but he can't move. Logically it makes sense, the fight, flight, or freeze instinct kicking in, but it was only an abstract fact before now.

Dean wraps a hand around Cas' upper right arm and pulls him out. Cas gets his feet under him, but he feels numb, like he's walking on a cloud. He's breathing too fast, but he can't make himself calm down.

All he can picture in his mind is what he saw when he pulled Dean from Hell all those years ago, because he saw it all. Every bit of Dean's life, the good and the bad, was right there. He remembers a cocky, teenage Dean who thought he knew better than his father and found himself pulled over John's knee more than a few times. Dean was a stubborn kid, but spankings worked when nothing else did, so that's what he got.

Cas knows what it's like through Dean's eyes. He may never have experienced it as a human himself, but he knows it'll hurt in more ways than one. He knows Dean's going to make it count because what Cas did, what he's been doing can't be ignored.

He suddenly gasps, and he doesn't know how long he'd been holding his breath, but now he can't get enough oxygen. He's panting, and he thinks he can hear himself whimpering as Dean pulls him up the stairs.

_"You know what that means, Cas? Do you realize I'm gonna toss you over my knee, yank your pants and boxers down, then smack your ass? I'm gonna keep going until you're crying and begging me to stop. And it's not gonna be because I'm pissed or I'm looking for revenge. It's because what you're doing is hurting you and could get you killed, and I'm not gonna let you do that."_

Dean doesn't use words to say how he feels about someone. He shows it. He chooses his words carefully and if someone's watching, paying attention, they'll know. Cas knows. Dean loves him and considers him family. He wouldn't care about Cas running off and doing stuff like this if he didn't love him.

Cas' chest feels tighter and his eyes are burning, his lips feel tingly and like they want to move without his consent. Not to talk, but they're quivering, and Cas has seen humans do this, but never really understood how it felt before.

Dean takes him into the kitchen and stops at the steel counter where they have some cooking utensils. He pulls out a wooden spoon, and just as Cas starts to pull back, his ass clenching at just the thought of it being used on him, Dean drops the spoon back into the jar and grabs another utensil.

Cas decides he wants the spoon instead. Because the thing that Dean pulls out is thicker, more sturdy, and the head of the thing will cover about twice the diameter the spoon would have. Worst of all, it's old and well-worn, which means there won't be any give. Cas shakes his head, mouth opening even though he doesn't know what to say, but Dean makes up his mind, and then they're walking out of the kitchen.

Dean walks into Cas' room, leaves the door open, and doesn't stop until he's standing by the right side of the bed. Cas is ready for the discussion. He wants it. It'll buy him some time. Whenever Dean got tossed over his dad's knees, there was a discussion first, and Dean would prolong it, but Cas never knew why before he was standing by the bed, hoping for anything to happen that would give him more time.

Cas stands there while Dean pulls Cas' jacket off. He doesn't know or care where Dean puts it. He feels vulnerable in just his jeans, T-shirt, socks, and boots. It's silly, and he doesn't know why the jacket felt like a protection.

Dean unbuttons Cas' jeans, then sits down on the bed, so Cas moves to sit down next to him, but is surprised when Dean yanks him by the left arm and pulls him down over his lap.

Cas lets out a noise that mimics an animal in distress, and it shocks him for a moment, but then he feels his jeans and boxers coming down and fear flares bright and painful in his chest, his stomach.

"Dean!" Cas yelps, twisting as he pushes back, but Dean holds him down, and while he knows it's not effortless to hold a grown man down, Cas can't help but feel trapped and weak.

"Settle down," Dean says, voice gruff. "You're not gettin' up for a long time."

Cas gasps as the spoon connects. It's the sound more than the pain that gets to him. He wasn't expecting it, and as the pain blossoms out from the middle of his right ass cheek, everything suddenly becomes even more real.

He's over Dean's lap. His jeans and boxers are around his ankles. Dean's got the upper hand and in this position he's stronger than Cas. He's using a wooden spoon that Cas is sure he's going to burn once this is over.

Dean's hitting him.

Dean was upset enough over this whole thing that he's actually spanking him, and Cas finally understands why Dean used to start crying even before the spanking started. His chest aches, it's hard to breathe, and squirming does absolutely nothing to make the pain in his backside better, but he can't stop himself, can't hold still.

It's silent in the room other than the sound of the spoon hitting his ass and his own breathing and whimpering, so when he cries out, legs kicking and hands scrabbling for anything that could get him off of Dean's lap, it feels too loud, and he wants Dean to make some noise too, but he doesn't know why.

He manages to get his right leg up and over Dean's and pushes himself toward the head of the bed, his cock dragging painfully over the material of Dean's jeans.

"No! No, Dean, please!" Cas yells as Dean wraps his left arm around Cas' middle and brings him right back into position.

He wants to see Dean's face. He wants Dean to say something. Anything. He wants it to stop. He wishes he'd never even considered putting himself in this position. It wasn't worth it.

"I'm sorry!" Cas wails, yanking at the blanket and sheet.

Cas feels the grip on his waist loosen and takes advantage of it, throwing himself onto the floor. He regrets it instantly when his ass lands hard, his momentum causing his sore skin to drag on the rough flooring. He's panting as he looks up at Dean.

"You're sorry?" Dean asks, and his voice is quiet.

"I'm really sorry! I won't do it again!" Cas says, shaking his head.

"What are you sorry for?" Dean asks, tapping his leg with the spoon. It's a casual movement that unnerves Cas even more.

"I'm sorry I lied," Cas says, trying to catch his breath.

"Is that all?" Dean asks.

Cas squirms. He knows there's more, but he doesn't want to say it. Saying it out loud makes it more real, and he never understood it before he lost his grace and became human like Dean.

"C'mere, we're not done," Dean says, patting his leg with his left hand.

"No!" Cas says, eyes widening as he holds his hands up. "There's more. I lied about where I was and I left while you and Sam weren't here so you wouldn't stop me."

"And what did you do?" Dean asks, brow furrowing. "What really important and dangerous thing that I told you not to do did you go ahead and do?"

"I don't know why you're asking," Cas says, face screwing up in confusion. "You know what I did and-"

"One," Dean says, interrupting Cas.

"One?" Cas asks, even more confused.

"Two," Dean says.

Cas remember this. He suddenly and clearly remembers what it means and scrambles to his knees. "Wait! Wait! You're doing it to make sure I understand what I've done wrong!"

Dean nods. "Yup. Beating your ass is just abuse unless you know why we did this. I'd rather not have to do this again in the future, so I want to know you fully understand why."

Cas thinks about it a moment, and then he feels a flare of anger. "I'm doing what you and Sam do all the time."

Dean crosses his arms over his chest and tilts his head a bit. "This isn't about me or Sam."

"It is when I'm out there following leads just like you do," Cas says.

"Oh, I see," Dean says, nodding. "So when you're following one of Crowley's minions around without telling us what you're doing, that's the same as what we do."

"Yes," Cas says, resting on his ankles, then quickly deciding that wasn't a good idea because it really hurt.

"And when you ditch us to trade things you've stolen from the bunker," Dean says, pausing as Cas squirms, "to trade for information, that's something else we've done?"

"You would," Cas says.

Dean lets out a huff of laughter. "And when you purposely curse yourself with an object that makes you stronger while simultaneously lowering your inhibitions, that's something we've done?"

Cas nods. "You would," he says again.

"No," Dean says, "I wouldn't."

"If Sam's life were in danger-"

"Your life isn't in danger," Dean interrupts. "What you're going after, you're not going to get back without signing up for something that isn't worth the risk."

"You can't say that," Cas hisses.

"Like Hell I can't," Dean says, voice louder than before. "You lost your grace, and that sucks really fuckin' bad, and if I could change it for you, I would. But you know just as well as I do that the way you're going about this is wrong, and it's going to get you killed."

"I just needed one more-"

"Yeah, that's how it always is," Dean says. "One more of this, a little more of that, and because it's one step at a time, you don't notice how far you've gone. And this isn't the first time Sam and I have had to track you down. It _is_ the first time we had to bribe a witch to take a curse off you because of it."

"So this is the solution?" Cas challenges.

"No, this isn't a solution," Dean says, shaking his head. "This is a reminder and incentive to stop doing the shit you're doing. We do this together. We don't lie to each other, go behind each other's backs, hitchhike across the country, and follow a demon to visit a witch."

Cas knows it sounds bad when Dean puts it like that, but he just can't let it drop. "Are you enjoying this?"

"I don't _want_ to do this," Dean says, and Cas can see the regret in his eyes. "C'mere," Dean says, holding out his hand.

Cas frowns at him. "Why?"

"So we can finish up here," Dean says.

Cas' eyes widen. "You already spanked me!"

"No, what I did was get your attention," Dean says. "I want to make sure this leaves a lasting impression so we don't have a repeat performance."

"It won't happen again," Cas says, then gasps as Dean stands up heading for him. "No! Wait! Dean, no!"

Cas tries to pull away, but Dean pushes him down onto his stomach, flat on the floor, and grabs his flailing right arm, holding his wrist at the small of his back.

"No! No! Dean, stop!" Cas screams as Dean hits him harder than before with the spoon.

Cas twists this way and that, boots smacking into the desk and possibly knocking some things over, but it doesn't do him any good. He bends his knees, bringing his feet up and trying to cover his ass. Cas thinks he's won because Dean stops, but then Dean's pulling him up and dragging him over to the bed.

Dean gets them up onto the bed and pulls Cas over his lap again, bringing the spoon down over and over again. Cas' ass hurts so much he lets out a bleat of frustration and pain.

"I w-ow! I won't do it again!" Cas yells, yanking at the blanket and sheets, hoping to get some leverage, but Dean's got him.

He feels helpless and scared, and he feels very, very sorry. It's different than before. Before he just wanted Dean to stop, and he still wants that, but now he thinks about Dean, how Dean isn't doing this because he feels like it, but because he cares about Cas and worries about him. It hurts even more.

Cas bends his knees, trying to cover his ass again, remembering how well it worked when Dean had him on the floor, and when Dean stops Cas thinks he's been successful, but then Dean repositions him, pushing his legs down and locking them with his own right leg.

"No!" Cas howls as Dean starts spanking him again. "I said I wouldn't do it again! Please! Dean! Dean, stop! Dean!" he cries out, vision blurring with tears.

He lets out a sob, squeezing his eyes shut and flailing, and when he tries to suck in more air, he can't. It's stuck. He's never going to be able to breathe again, and he needs to now that he's a human. He panics, mouth open in a silent scream, but his lungs won't work.

Dean thumps him on the back, and it's enough of a shock that Cas can suddenly breathe again. He sucks in the air, almost choking on it, and then he's crying. Heaving sobs that seem to come from deep inside him, and he can't cry hard enough, can't get in enough air, and he doesn't know why this has to be so hard.

It takes him a moment to realize Dean's not spanking him anymore, and he cries even harder because it's over and he lived and he never knew it could be like this.

Dean's rubbing his back, but it's not enough. Cas wants to be closer. Needs to be. He twists, grabbing Dean's shoulder and half climbing him, half pushing him down to the bed, and then he's straddling Dean and burying his face in Dean's neck, sobbing and not caring one bit that he's getting snot and tears all over Dean.

Cas shudders as Dean wraps his arms around him, his hands smoothing over Cas' back, and it feels so good that Cas starts crying harder, but he doesn't know why.

"Hey, hey, I gotcha," Dean says softly.

"I don't w-want any more," Cas blubbers into Dean's neck.

"You're not getting any more," Dean says. "You were punished, and I forgive you."

Cas melts against Dean, body going lax as he sniffles. "I'm sorry."

"I know," Dean says.

"I didn't like that," Cas says.

Dean lets out a huff of laughter. "Neither did I."

"I really don't want it to happen again," Cas says, wiping his nose on Dean's shoulder.

Dean lets him, doesn't get upset with him for it. "I don't want it to happen again either."

"Can I burn the spoon?" Cas asks. Cas frowns at Dean's chuckling. "I mean it. I want to burn it."

"I don't know," Dean says, "it was the perfect tool for the job."

"I'm burning it," Cas says.

Dean chuckles again. "Okay. We'll burn it later."

"Do I get to sleep with you tonight?" Cas asks.

Dean pauses. "Huh?"

"You always crawled into bed with Sam after you got spanked," Cas says. "It made you feel better."

"It did," Dean says, "and you can."

"I'm never going to be able to sit down again."

Dean chuckles. "You'll be fine. It'll hurt tonight and you'll still be somewhat sore tomorrow, but in a few days you won't even remember this."

Cas gets his hands on Dean's chest and pushes himself up so he can glare at Dean. "I won't be forgetting this."

Dean smiles. "I know."

Cas' stomach growls. "I'm really hungry," he says as if his stomach has betrayed him by requiring food.

"Yeah, well, you worked up an appetite flopping around over my lap," Dean says.

Cas carefully slides off of Dean, making sure his ass doesn't rub against any material on the way. He bends over to pull his boxers and jeans up, but Dean sits up and holds out a hand.

"Wait," Dean says, then gets up and heads for Cas' drawers. He pulls one open, then another until he finds a pair of sleep pants, then hands them to Cas. "These'll feel better."

"Oh, thank you," Cas says.

"Here, lemme help you," Dean says as he crouches down and unlaces Cas' boots.

Cas straightens, watching as Dean takes the time to lift each foot and take each boot off, then helps him step out of the jeans and boxers.

"I always get a little shaky," Dean says as he takes the sleep pants from Cas and holds them out for Cas to step into.

Cas smiles crookedly as Dean carefully slides them up his legs, avoiding his ass.

"There, all set," Dean says. "Do you know what you want to eat?"

Cas thinks about it a moment, then grins. "One of those sandwiches you made Sam the other night. With the marshmallow fluff and peanut butter."

Dean chuckles. "I don't know how you guys eat those," he says, shaking his head, but he's clearly amused. "Okay, but what if Sam brought home something better?"

"I can eat both," Cas says. "I'm very hungry."

Dean puts his hands on Cas' shoulders from behind and guides him out of the bedroom. "Sounds good to me."

"Can we watch a movie tonight?" Cas asks as they make their way to the kitchen. "I saved a few movies on Netflix that looked interesting."

Dean wraps his left arm around Cas as they walk into the kitchen, Sam already there and brow furrowed in concern. "Yeah, we'll make Sam set the laptop up in my room."

"Thank you, Dean," Cas says, then leans over the steel table, ready to watch as Dean makes his sandwich.


	40. Do You Want to Come?

**Summary for the Chapter:**

> **Rieraclaelin's Request:** May I ask for a prompt? I know you have a lot more ahead of mine, but, if you feel like doing it, I would be totally ok with it! ;) (and if you've already done one like it, just ignore it!) May I have a Sastiel d/s type prompt, with a lot of Cas edging Sam with any kinds of toys, as well as possibly some grace kink! type edging? Basically until Sam is nothing but a whimpering, incoherent mess before Cas lets him come? Also, I wouldn't object to any spanking and panties!

**Notes for the Chapter:**

>  **Warnings:** None
> 
>  **Tags for This Chapter:** Sam/Castiel, bondage, mild D/s, edging, begging, mild spanking, toys/plugs, handjob, blowjob, panties, mild pain play, grace play, dirty talk

Sam doesn't know how long it's been. It feels like forever that he's been immobile, strapped onto a bondage chair, comfortable yet secure, arms out at his sides at shoulder level, legs spread, head against the padded headrest.

The cute little pink mesh panties with black trim are soaked with sweat and the lace has rubbed a sore spot behind his balls because he just can't sit completely still, and Cas has been keeping him on edge, nearly mindless for hours or days or years.

The last thing Cas used on him was a sleeve attached to a vibrator, and Sam lost count of how many times he'd almost come only to thrash about and whimper as Cas stopped all stimulation, backing him off again.

There's a vibrating butt plug in his ass that Cas turns on at random times, and he thinks he might finally be losing his mind because he swears there's something trailing over his dick, but he can't see anything, and Cas is nowhere near him.

Cas is across the room, leaning against the desk. Sam's desk in Sam's room. It's a mindfuck in and of itself because this is where he sleeps. Researches. Watches movies with Cas while they sit on the bed, elbows rubbing against one another as Cas flicks jelly beans at him.

Sam gasps as something rubs over the tip of his dick, and for a moment he's scared. He's seen enough bad shit in his life that there could be any number of things on his dick, but he looks up at Cas again and his body relaxes.

Cas isn't alarmed. He isn't upset. And he isn't running across the room to kill whatever creature has decided to tease Sam's piss hole. Which means Cas is doing it.

"Oh, fuck," Sam moans, his head dropping back on the padded head rest.

Sam has always believed in angels. They were something fascinating and beautiful, and even though he's come to think of Cas as his friend and lover, he still can't help but feel a sense of awe.

An angel is driving him wild, touching him, using his grace to make Sam squirm and cry out. Sam almost comes right then and there, but something pinches his balls.

"Ah! Cas, please! Please!" Sam begs as he gives Cas his best 'you know you wanna let me come' face.

Cas doesn't say anything, and Sam doesn't know if he can take any more. His muscles are cramping and his dick is so hard, so red that even the soft breeze created by Cas walking by him makes his skin tingle. He feels even more exposed with Cas still in slacks, a button-down shirt, and socks.

Sam bites his lip as Cas flicks a nipple. Cas walks around behind the chair, and Sam shivers because his ass is hanging out in the air, waiting for Cas to do whatever he wants. The bondage chair supports his thighs, back, and arms, but Cas has access to everything else.

He hears the smack before he feels it and squeezes his eyes shut, because even though it's not over the butt plug, it jostles the plug inside him. The burn of the smack makes his teeth clench, and he braces himself for the next one on the other cheek, but it still makes him cry out, makes more precome ooze out of his cock.

Sam loves to be at the mercy of Cas. To give himself over to someone willingly. Someone he trusts won't abuse that power. Someone who wants Sam to feel good. Someone who knows exactly what Sam likes and doesn't like. Someone who loves him enough to hold him afterward, kissing him and telling him how proud he is of Sam.

Cas runs the tips of his fingers over Sam's right arm and down his torso as he walks around to face Sam, then kneels between his legs, resting his arms on thighs.

"Do you want to come, Sam?" Cas asks as if he doesn't know.

"Yes," Sam says, nodding. His sweat-soaked hair falls in his eyes, and Cas reaches up, pushing his hair back. "Please, Cas. Please."

"You look so good here," Cas says, that intense stare directed at Sam. "In your pretty pink panties," he says as he runs a finger over the material bunched under his balls.

Sam gasps, the pain enough to make him squirm. He drops his head back on the headrest and whimpers as the tingling inside his dick starts up again. He hasn't paid attention, can't remember when it stopped, but it's going again and almost feels like waves. His brain can't really comprehend it.

"Ah! Fuck, Cas, oh fuck!" Sam cries out as the plug in his ass vibrates on high, but this time the same sensation is inside his dick.

The only thing that keeps him from going over the edge is the firm tug on his balls just before it all dies down again, leaving Sam panting. He blinks up at the ceiling, his whole body trembling.

"Do you want to come, Sam?" Cas asks.

Sam lifts his head and looks Cas in the eye. "Yes. Please, Cas. Hurts. It fuckin' hurts."

"What hurts?" Cas asks.

Sam huffs out a laugh that's almost hysterical. Cas can tell exactly what hurts. He can see everything, can look deep into Sam. Sees the damaged soul and the meat suit holding it in. Cas knows, but he wants Sam to talk to him because he likes to hear Sam's breathy, aroused voice.

"Under my balls," Sam says, because that's the worst thing at the moment. "And my dick. And my balls. And my ass from where you spanked me," he says, adding a little pout for emphasis.

Cas smiles. "Do you want me to stop?" he asks.

"No!" Sam blurts.

He learned the first time they played what stopping means. It doesn't mean Sam gets to come. It means Cas unties him and they cuddle for a while in bed, and even though Sam really, really wants to snuggle up to Cas and feel safe and loved in his arms, he wants to come first.

"What do you want?" Cas asked.

Oh, yeah. Sam feels silly for not realizing. He'd been so lost in the sensations that he'd forgotten one of the reasons Cas does this in the first place.

"Want you to make me come," Sam says. "I want you to play with me as much as you want, and then I want you to... I want you to make me come. Wanna come so fuckin' bad, Cas. Please. And after I come, after you make me scream, I want you to get yourself off. I wanna watch you come. I want you to come all over me."

Cas leans forward and licks the underside of Sam's cock, making him whimper. Cas' tongue flicks over the little bundle of nerves just under the head of Sam's cock as his fingers pinch and twist the skin of Sam's balls.

"Ah, shit. Shit. Cas, that fuckin', ah-ow," Sam whines, trying to close his legs even though he knows he can't. Not the way Cas has him tied.

Sam howls as the plug in his ass starts again just as Cas squeezes his balls. He thrashes on the chair, toes curling and his skin getting sore wherever he's bound.

All the sensation stops, and Sam blinks the tears out of his eyes as he looks down at Cas.

"Do you want to come?" Cas asks.

Sam lets out a noise of frustration. Almost a growl. "Yeah. I wanna come," he says through clenched teeth. "I don't know what you want me to say, Cas."

Something brushes over his nipples. It's like a gust of wind, and it startles him for a moment, but then he moans. He has a sudden desire to run out of the bunker and tell everyone he encounters that an angel can drive him wild with his grace. That Cas uses something supernatural to play him so expertly.

"Sam," Cas says.

"Yeah, Cas," Sam says, nodding. "I'm here." And he knows he wasn't for a moment. Knows that Cas could tell. Probably even knows what he was thinking about. Cas wants him there with him. So Sam nods again, clearing his mind of anything but Cas. "I'm here."

"Good boy," Cas says. "Do you want to come?"

Sam thrashes about, so frustrated that he lets out a scream, slamming his head back against the headrest. "Yes! I want to come! Just like all the other times I said I wanted to come. I still want to-ah!" he yelps as Cas starts sucking his cock.

He's so hard that the suction almost hurts, but it feels amazing, and Sam never wants it to stop. He tries to thrust up into Cas' mouth, but he's too tightly bound to the chair.

"Please lemme come, please!" Sam babbles. He thinks maybe he says other things, but he's too lost. He's too turned on and desperate.

Cas isn't hurried. The suction is almost inhuman, but his head bobs at a slow pace, and Sam wishes he could break through the restraints and grab Cas' head, fuck his face and come down his throat.

Just the thought of doing that to Cas, doing that to an angel pushes him closer to the edge than he's been all night, and as his balls pull up tight against his body, he bites his lip, hoping and praying that Cas doesn't realize he's so close. That he's about to come.

"Ah! Fuck, Cas, no! No! Fuck!" Sam screams, not giving a fuck if his voice carries outside the room because Cas is flicking his balls, his mouth no longer wrapped around Sam's cock.

Cas flicks his balls until Sam lets out a sob, tears running down his cheeks. Tears of frustration and pain.

"Do you want to come?" Cas asks, flicking his balls one more time.

"Yes!" Sam screams, yanking forward in the restraints, and whether he's trying to intimidate Cas or just get his point across isn't really clear in his head, but he just knows he wants it. "I want to fucking come! I want to come! If you didn't fuckin' hear me the first thousand times, I'll say it again. I. Want. To. Come."

Cas starts stroking his cock. It's fast, and his hand is so tight around Sam's cock that Sam feels himself almost going over the edge again. He doesn't know what his body's doing. He doesn't know what he should say or if Cas is ever going to let him come.

"Please, please, please," Sam chants, squeezing his eyes shut and willing Cas to just let him come, and then it stops. "No! No! Cas, fuckin'... No! I wanna fuckin' come! Just let me come! Please, Cas!"

"Do you want to come?" Cas asks.

Sam's nerves are on fire, and he lets out a noise that sounds like a dying animal as he yanks and kicks and shakes and screams. When he finally settles, panting and shaking so badly that he doesn't think he could stand if he had to, Cas is there, looking up at him with no expression on his face, but his hand is moving on Sam's dick, the pressure just right, the speed just right, and Sam doesn't want to hope, but he can't help it.

Cas kisses his inner thigh, mouths his way over to Sam's balls and sucks. Sam babbles, but he doesn't even know what he's saying. He thinks he begging, but he can't even make his mouth move right, and when the sensation inside his dick starts up again, it's too much. His balls ache as he comes, his cock jerking so hard he'd be impressed if it weren't for the fact he's gone.

He thrusts up, fucking Cas' hand as best he can, hands balled into fists and toes pushing against the cement flooring. When he done, his body collapses against the chair. He blinks at the ceiling, his stomach convulsing with the aftershocks, and his panting breaths are almost not enough.

Sam doesn't notice what's going on until he's in bed, his body clean and the plug out of his ass. The restraints are gone, and Cas is snuggling up to him, putting his head down on Sam's shoulder and wrapping his right arm around Sam's chest.

Cas places gentle kisses on Sam's neck and shoulder, and Sam feels so warm, so content and boneless that he almost can't keep his eyes open. He can tell the panties are gone, and the spot under his balls is healed.

He remembers that conversation he had with Cas months ago. About how frustration has always made him come really hard, but he's never had anyone frustrate him as much as Cas has, and even though it's not something Sam would want to do all the time, Sam feels pride swell in his chest, because Cas did that for him. He had listened and used everything he knew about Sam to give him one of the best orgasms he'd ever had.

"I love you, Sam," Cas whispers, then kisses him on the cheek before settling down.

"Love you too, Cas," Sam replies, already half asleep.


End file.
